← Back to Patent Explorer
US4221876A Expired / Lapsed US ⏱️ 0.0 years remaining

Isocyanate-reactive mixtures based on formose

Assignee: Bayer AG
•
Filing: 1978-08-17
•
Granted: 1980-09-09
•
Expires: 1998-08-17
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract This invention relates to mixtures, in the form of relatively low viscosity liquids at room temperature, of formose, aldehydes and/or ketones aldolated in the α-position and, optionally, water and/or crystalline mono- or di-saccharides, and to the use of these mixtures for the production of polyurethane plastics, particularly foams.

Inventors

  • 👤 Kuno Wagner

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 11:20
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/32; C08G18/3203; B; B01; B01J; B01J19/00; B01J19/24; B01J19/245; B01J19/2455; B01J19/2465; C07; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/14; C07C29/36; C07C29/38; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C45/75; C07H; C07H3/00; C07H3/02; C08G6/00; C08G6/02; B01J2219/00; B01J2219/00002; B01J2219/00027; B01J2219/0004

Claims Analysis

Total Claims: 36
Claim 1
Independent Claim 85 words
Isocyanate reactive mixtures comprising (a) from 20 to 90% by weight, based on (a)+(b), of a mixture of polyhydric alcohols, hydroxy aldehydes and hydroxy ketones which have been obtained by the condensation of formaldehyde hydrate (b) from 10 to 80% by weight, based on (a)+(b), of aldehydes and/or ketones methylolated in the α-position and incapable of enediol formation (c) from 0 to 50% by weight, based on (a)+(b), of water, and (d) from 0 to 100% by weight, based on (a)+(b), of monosaccharides and/or disaccharides.
Claim 2
Dependent Claim 85 words
Isocyanate reactive mixtures comprising (a) from 20 to 90% by weight, based on (a)+(b), of a mixture of polyhydric alcohols, hydroxy aldehydes and hydroxy ketones which have been obtained by the condensation of formaldehyde hydrate (b) from 10 to 80% by weight, based on (a)+(b), of aldehydes and/or ketones methylolated in the α-position and incapable of enediol formation (c) from 0 to 50% by weight, based on (a)+(b), of water, and (d) from 0 to 100% by weight, based on (a)+(b), of monosaccharides and/or disaccharides.
Claim 3
Dependent Claim 39 words
The mixtures of claim 1 wherein component (a) comprises from 40 to 70% by weight, component (b) comprises from 25 to 60% by weight, and component (c) comprises from 0.3 to 30% by weight, all weights based on (a)+(b).
Claim 4
Dependent Claim 18 words
The mixtures of claim 2, wherein component (c) comprises from 0.8 to 10% by weight based on (a)+(b).
Claim 5
Dependent Claim 18 words
The mixtures of claim 2, wherein component (d) comprises from 10 to 50% by weight, based on (a)+(b).
Claim 6
Dependent Claim 40 words
The mixtures of claim 1 wherein component (a) comprises formoses having an average molecular weight of from 92 to 360 and a sugar content, expressed as glucose having a molecular weight of 180, of from 4 to 85% by weight.
Claim 7
Dependent Claim 29 words
The mixtures of claim 5, wherein said formoses have an average molecular weight of from 100 to 240 and a sugar content of from 6 to 72% by weight.
Claim 8
Dependent Claim 23 words
The mixtures of claim 1, wherein component (b) comprises aliphatic, cycloaliphatic, or araliphatic aldehydes and ketones containing from 2 to 15 carbon atoms.
Claim 9
Dependent Claim 17 words
The mixtures of claim 7, wherein said aldehydes and ketones contain from 2 to 9 carbon atoms.
Claim 10
Dependent Claim 16 words
The mixtures of claim 1, wherein component (b) is selected from the group consisting of ##STR7##
Claim 11
Dependent Claim 25 words
The mixtures of claim 1, wherein the aldehydes and/or ketones of component (b) are selected from the group consisting of n-butyraldehyde, isobutyraldehyde, acetone and cyclohexanone.
Claim 12
Dependent Claim 141 words
A process for producing isocyanate-reactive mixtures comprising condensing aqueous formalin solutions and/or paraformaldehyde dispersions containing from 20 to 65% by weight of formaldehyde at pH-values of from 4 to 9 and at a reaction temperature of from 70° to 110° C. in the presence of (a) soluble or insoluble salts of metals of the Second to Fourth Main Group or of the First to Eighth Secondary Group of the Periodic System of Elements or metal ions of said groups and/or subgroups fixed to a high molecular weight support, (b) aldehydes and/or ketones capable of α-aldolation or their α-methylolation products and, optionally (c) co-catalysts based on compounds capable of enediol formation, until the residual formaldehyde content is from 0 to 10% by weight, based on the reaction mixture; subsequently removing the catalyst; and concentrating the reaction product to the desired water content.
Claim 13
Dependent Claim 141 words
A process for producing isocyanate-reactive mixtures comprising condensing aqueous formalin solutions and/or paraformaldehyde dispersions containing from 20 to 65% by weight of formaldehyde at pH-values of from 4 to 9 and at a reaction temperature of from 70° to 110° C. in the presence of (a) soluble or insoluble salts of metals of the Second to Fourth Main Group or of the First to Eighth Secondary Group of the Periodic System of Elements or metal ions of said groups and/or subgroups fixed to a high molecular weight support, (b) aldehydes and/or ketones capable of α-aldolation or their α-methylolation products and, optionally (c) co-catalysts based on compounds capable of enediol formation, until the residual formaldehyde content is from 0 to 10% by weight, based on the reaction mixture; subsequently removing the catalyst; and concentrating the reaction product to the desired water content.
Claim 14
Dependent Claim 31 words
The process of claim 11, wherein said pH-value is from 5 to 8, and wherein the condensation is continued until the residual formaldehyde content is from 0.5 to 6% by weight.
Claim 15
Dependent Claim 157 words
A process for producing isocyanate-reactive mixtures comprising condensing aqueous formalin solutions and/or paraformaldehyde dispersions containing from 20 to 65% by weight of formaldehyde at pH-values of from 4 to 9 at a reaction temperature of from 70° to 110° C. in the presence of (a) soluble or insoluble salts of metals of the Second to Fourth Main Group or the First to Eighth Secondary Group of the Periodic System of Elements or metal ions of said groups and/or subgroups fixed to a high molecular weight support, and (b) co-catalysts based on compounds capable of enediol formation, up to a conversion of from 40 to 95% by weight, based on the formaldehyde used, to form mixtures of low molecular weight polyhydric alcohols, hydroxy aldehydes and hydroxy ketones; binding the residual formaldehyde by the addition of α-aldolatable carbonyl compounds incapable of enediol formation; freeing the reaction product from the catalyst; and concentrating reaction product to the desired water content.
Claim 16
Dependent Claim 157 words
A process for producing isocyanate-reactive mixtures comprising condensing aqueous formalin solutions and/or paraformaldehyde dispersions containing from 20 to 65% by weight of formaldehyde at pH-values of from 4 to 9 at a reaction temperature of from 70° to 110° C. in the presence of (a) soluble or insoluble salts of metals of the Second to Fourth Main Group or the First to Eighth Secondary Group of the Periodic System of Elements or metal ions of said groups and/or subgroups fixed to a high molecular weight support, and (b) co-catalysts based on compounds capable of enediol formation, up to a conversion of from 40 to 95% by weight, based on the formaldehyde used, to form mixtures of low molecular weight polyhydric alcohols, hydroxy aldehydes and hydroxy ketones; binding the residual formaldehyde by the addition of α-aldolatable carbonyl compounds incapable of enediol formation; freeing the reaction product from the catalyst; and concentrating reaction product to the desired water content.
Claim 17
Dependent Claim 28 words
The process of claim 13 wherein the condensation in continued up to a conversion of from 70 to 90% and wherein the pH-value is from 7 to 9.
Claim 18
Dependent Claim 22 words
The process of claim 13 wherein said pH-value is from 5 to 8, and wherein said conversion is from 70 to 90%.
Claim 19
Dependent Claim 54 words
A process for producing isocyanate-reactive mixtures comprising mixing (a) an aqueous or alcoholic solution of a mixture of low molecular weight polyhydric alcohols, hydroxy aldehydes and hydroxy ketones, which have been obtained by the autocondensation of formaldehyde hydrate with (b) α-aldolatable carbonyl compounds; and subsequently methylolating the mixture by the addition of aqueous formaldehyde.
Claim 20
Dependent Claim 54 words
A process for producing isocyanate-reactive mixtures comprising mixing (a) an aqueous or alcoholic solution of a mixture of low molecular weight polyhydric alcohols, hydroxy aldehydes and hydroxy ketones, which have been obtained by the autocondensation of formaldehyde hydrate with (b) α-aldolatable carbonyl compounds; and subsequently methylolating the mixture by the addition of aqueous formaldehyde.
Claim 21
Dependent Claim 27 words
The process of claim 16 wherein from 20 to 300% of the quantity of formaldehyde required to obtain complete methylolation of the α-aldolatable carbonyl compound is added.
Claim 22
Dependent Claim 27 words
The process of claim 17, wherein from 50 to 150% of the quantity of formaldehyde required to obtain complete methylolation of the α-aldolatable carbonyl compound is added.
Claim 23
Dependent Claim 28 words
The process of claim 17 wherein the methylolation reaction is conducted to a pH of from 7 to 9 and a temperature of from 10° to 65° C.
Claim 24
Dependent Claim 22 words
The process of claim 19, wherein the pH-value is from 7.5 to 8 and the temperature is from 20° to 50° C.
Claim 25
Dependent Claim 14 words
The process of claim 16 wherein following the methylolation reaction excess water is removed.
Claim 26
Dependent Claim 34 words
The process of claim 21 wherein the excess water is removed in a thin-film evaporator under a vacuum of from 1 to 18 Torr and at a temperature of from 35° to 60° C.
Claim 27
Dependent Claim 144 words
A process for the production of optionally cellular polyurethane plastics comprising reacting (a) polyisocyanates with (b) polyhydroxyl compounds having a molecular weight of less than 400, optionally (c) polyhydroxyl compounds having a molecular weight of from 400 to 10,000 and, optionally, other isocyanate-reactive compounds, optionally in the presence of (d) blowing agents, catalysts, and fillers wherein component (b) comprises an isocyanate-reactive mixture comprising (a) from 20 to 90% by weight, based on (a)+(b), of a mixture of polyhydric alcohols, hydroxy aldehydes and hydroxy ketones which have been obtained by the condensation of formaldehyde hydrate, (b) from 10 to 80% by weight, based on (a)+(b), of aldehyde and/or ketones methylolated in the α-position and incapable of enediol formation (c) from 0 to 50% by weight, based on (a)+(b), of water, and (d) from 0 to 100% by weight, based on (a)+(b), of monosaccharides and/or disaccharides.
Claim 28
Dependent Claim 144 words
A process for the production of optionally cellular polyurethane plastics comprising reacting (a) polyisocyanates with (b) polyhydroxyl compounds having a molecular weight of less than 400, optionally (c) polyhydroxyl compounds having a molecular weight of from 400 to 10,000 and, optionally, other isocyanate-reactive compounds, optionally in the presence of (d) blowing agents, catalysts, and fillers wherein component (b) comprises an isocyanate-reactive mixture comprising (a) from 20 to 90% by weight, based on (a)+(b), of a mixture of polyhydric alcohols, hydroxy aldehydes and hydroxy ketones which have been obtained by the condensation of formaldehyde hydrate, (b) from 10 to 80% by weight, based on (a)+(b), of aldehyde and/or ketones methylolated in the α-position and incapable of enediol formation (c) from 0 to 50% by weight, based on (a)+(b), of water, and (d) from 0 to 100% by weight, based on (a)+(b), of monosaccharides and/or disaccharides.
Claim 29
Dependent Claim 15 words
The process of claim 23, wherein component (c) comprises from 4 to 25% by weight.
Claim 30
Dependent Claim 15 words
The process of claim 24, wherein component (c) comprises from 8 to 20% by weight.
Claim 31
Dependent Claim 14 words
The process of claim 23, wherein the isocyanate index is from 20 to 70.
Claim 32
Dependent Claim 14 words
The process of claim 26, wherein the isocyanate index is from 30 to 60.
Claim 33
Dependent Claim 14 words
The process of claim 27, wherein the isocyanate index is from 35 to 55.
Claim 34
Dependent Claim 15 words
The process of claim 23 wherein component (c) comprises from 0 to 4% by weight.
Claim 35
Dependent Claim 15 words
The process of claim 29, wherein component (c) comprises from 0.7 to 3% by weight.
Claim 36
Dependent Claim 21 words
The process of claim 23, wherein component (b) comprises from 5 to 30% by weight based on the total of (b)+(c).

References Cited (Backward Citations)

US2269935A Cited
US2760983A Cited
US3202620A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-09-09 1984-03-10 1984-09-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-09-09 1988-03-10 1988-09-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-09-09 1992-03-10 1992-09-09 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag