CH417084A - Process for hydrophilizing a polyurethane foam - Google Patents
Process for hydrophilizing a polyurethane foamInfo
- Publication number
- CH417084A CH417084A CH1160863A CH1160863A CH417084A CH 417084 A CH417084 A CH 417084A CH 1160863 A CH1160863 A CH 1160863A CH 1160863 A CH1160863 A CH 1160863A CH 417084 A CH417084 A CH 417084A
- Authority
- CH
- Switzerland
- Prior art keywords
- sub
- foam
- process according
- sultone
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 10
- 239000011496 polyurethane foam Substances 0.000 title claims description 10
- 239000006260 foam Substances 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000012442 inert solvent Substances 0.000 claims description 8
- 150000008053 sultones Chemical class 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 150000002576 ketones Chemical group 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- -1 inorganic acid anion Chemical class 0.000 claims description 2
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical group O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
- C08J9/40—Impregnation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
Procédé d'hydrophilisation d'une mousse de polyuréthane La présente invention a pour objet un procédé d'hy- drophiuisation d'une mousse de polyuréthane à base de polyester ou de polyéther.
Comme on le sait, les mousses alvéolaires se prê tent très bien à la fabrication d'éponges pour usage industriel ou .domestique. Les mousses de polyuré thane à cellules ouvertes, obtenues par réaction d'un polyisocyanate, sont sur un polyester, soit sur un poly- éther, présentent dans la plupart des cas l'apparence d'éponges naturelles.
Leur principal inconvénient, par rapport à ces dernières ou aux éponges à base de cellulose régénérée, est d'avoir un très faible pouvoir d'absorption d'eau.
L'invention a pour but d'éliminer cet inconvé nient des mousses de polyuréthane en fournissant un procédé qui permet de les rendre hydrophiles. Ce procédé est caractérisé par le fait que l'on fait réagir sur les groupes réactifs de la mousse au moins une sultane de la formule générale
EMI0001.0035
où n est un nombre entier au moins égal à 3, à une température comprise entre 601)
et 100o C et pendant un temps nécessaire à fixer chimiquement des molé- cuiles de la sultane sur les groupes réactifs de la mousse, après quoi on laisse refroidir celle-ci et on la lave.
Le procédé selon :l'invention consiste donc à ren dre une mousse de polyuréthane, ou une éponge pré parée à partir de cette mousse, hydrophile par addi- tion de molécules hydrophiles sur les groupes actifs de la mousse, par fixation chimique de ces molécu les. Cela peut être obtenu en imprégnant la mousse d'une solution de la sultane .dans un solvant inerte, en éliminant l'excès de solution et en chauffant la mousse imprégnée à la température désirée.
Il est à remarquer que dans ce texte on accorde le même sens aux termes mousse de polyuréthane et éponge en polyuréthane .
Comme sultane, -on peut utiliser, par exemple, la propane-sultone de la formule
EMI0001.0060
la butane-,sultone de la formule
EMI0001.0063
ou l'isobutane-sulto@ne, ainsi que toute autre sultane correspondant à la formule générale ci-dessus.
Comme solvant de la sultane, on peut utiliser le xylène, les cétones, les esters, les éthers, la .din6thyl- formamide et l'eau.
Quant à 'la température de réaction qui doit être comprise entre 600 et 100o C, les meilleurs résultats ont été obtenus avec une température d'environ 800 C.
Le procédé peut être mis en couvre, par exemple, de la manière suivante <I>Exemple 1</I> On imprègne la mousse de polyuréthane (ou une éponge en polyuréthane) d'une solution formée de 50 g -de propane-sultone dans 200 ml de xylène. Après avoir éliminé l'excès de solution, on chauffe à 80 C pendant une heure. On laisse refroidir et on lave.
La réaction selon !l'invention peut également être réalisée -en présence d'un catalyseur constitué par au moins un composé d'un métal alcalin de la formule générale M-A où M est un métal -alcalin et A un anion acide orga nique ou -inorganique, ou un reste alcoxy ou aryloxy. Ainsi, on peut utiliser, par exemple, les substances suivantes :
l'hydroxyde de potassium, l'hydroxyde de sodium, 1e mélange de ces derniers, d'acétate de potas- sium, le méthylate de potassium et l'isopropylat e de potassium.
La mise en oeuvre de cette variante du procédé, suivant laquelle on effectue la réaction en présence d'un catalyseur, peut être faite de deux manières : en un ou deux stades.
La mise en couvre en un stade consiste à impré gner la mousse d'une solution renfermant le cataly seur et la sultone, à éliminerl'excès :de solution et à chauffer la mousse ainsi imprégnée. Le lavage est effectué après refroidissement.
La mise en couvre en deux stades consiste à im prégner la mousse d'une solution du catalyseur, à éliminer d'excès de solution et à sécher, ceci consti tuant le premier stade.
Dans le :second stade, da mousse, sur laquelle le catalyseur a été ainsi préala blement déposé, est imprégnée d'une solution de sul- tone et chauffée après que l'excès de solution ait été éliminé. Le lavage est effectué après refroidissement comme précédemment.
Comme solvant du catalyseur, on peut utiliser Pmsopropanol ou le xylène, pour Pisopropylate et le méthylate de potassium, et l'eau pour .les hydroxydes de potassium et de -sodium et pour l'acétate de potassium.
Les exemples ci-après montrent la mise en couvre du procédé selon les variantes ci-dessus.
<I>Exemple 2</I> On .imprègne une éponge en polyuréthane d'une solution à 0,25 % d'isopropylate de potassium dans l'alcool isopropylique. On élimine l'excès de solution et on sèche.
On imprègne de nouveau la mousse d'une solution renfermant 15 % en poids d e propane-su@l- tone dans le xylène, et on chauffe à 800 C pendant une heure après avoir éliminé l'excès de solution. On laisse refroidir et on lave.
<I>Exemple 3</I> On procède comme dans l'exemple 2, mais en fai sant la première imprégnation avec une solution à 0,25% d'isopropylate de potassium -dans le xylène, la seconde avec une solution à 20% on -Poids de butane-sultone dans le diisobutyléther.
<I>Exemple 4</I> On procède comme dans l'exemple 2, mais en faisant la seconde imprégnation avec une solution à 25% en ponds de propane-sultone dans la diéthyd- cétone: <I>Exemple 5</I> On imprègne la mousse avec -une solution formée de 200 ml d'eau, 50g de propane-sultone, 4 g d'hy droxyde de potassium et 20 ml .dé @diméthyl-form- amide. On élimine l'excès de solution et on sèche.
On Go chauffe une heure à 800 C. On laisse refroidir et on lave.
Process for Hydrophilizing a Polyurethane Foam The present invention relates to a process for hydrophiising a polyurethane foam based on polyester or polyether.
As is known, cellular foams lend themselves very well to the manufacture of sponges for industrial or domestic use. Open cell polyurethane foams, obtained by reacting a polyisocyanate, are on a polyester or on a polyether, in most cases have the appearance of natural sponges.
Their main drawback, compared to the latter or to sponges based on regenerated cellulose, is that they have a very low water absorption capacity.
The object of the invention is to eliminate this drawback of polyurethane foams by providing a process which makes them hydrophilic. This process is characterized by the fact that at least one sultane of the general formula is reacted with the reactive groups of the foam.
EMI0001.0035
where n is an integer at least equal to 3, at a temperature between 601)
and 100 ° C and for a time necessary to chemically attach moleciles of the sultana to the reactive groups of the foam, after which the foam is allowed to cool and washed.
The process according to: the invention therefore consists in making a polyurethane foam, or a sponge prepared from this foam, hydrophilic by adding hydrophilic molecules to the active groups of the foam, by chemical attachment of these molecules. the. This can be achieved by impregnating the foam with a solution of the sultana in an inert solvent, removing the excess solution and heating the impregnated foam to the desired temperature.
It should be noted that in this text the same meaning is given to the terms polyurethane foam and polyurethane sponge.
As sultane, one can use, for example, the propane-sultone of the formula
EMI0001.0060
butane-, sultone of the formula
EMI0001.0063
or isobutane-sulto @ ne, as well as any other sultane corresponding to the general formula above.
As the solvent for the sultana, xylene, ketones, esters, ethers, dinethylformamide and water can be used.
As for the reaction temperature, which should be between 600 and 100o C, the best results have been obtained with a temperature of about 800 C.
The process can be carried out, for example, in the following manner <I> Example 1 </I> The polyurethane foam (or a polyurethane sponge) is impregnated with a solution formed from 50 g of propane-sultone in 200 ml of xylene. After removing the excess solution, the mixture is heated at 80 ° C. for one hour. Allowed to cool and washed.
The reaction according to the invention can also be carried out in the presence of a catalyst consisting of at least one compound of an alkali metal of the general formula MA where M is an alkali metal and A is an organic acid anion or - inorganic, or an alkoxy or aryloxy residue. Thus, the following substances can be used, for example:
potassium hydroxide, sodium hydroxide, a mixture of these, potassium acetate, potassium methoxide and potassium isopropylate.
The implementation of this variant of the process, according to which the reaction is carried out in the presence of a catalyst, can be carried out in two ways: in one or two stages.
The covering in one stage consists in impregnating the foam with a solution containing the catalyst and the sultone, in removing the excess: of solution and in heating the foam thus impregnated. Washing is carried out after cooling.
The covering in two stages consists of impregnating the foam with a solution of the catalyst, removing excess solution and drying, this constituting the first stage.
In the second stage, a foam, on which the catalyst has thus been previously deposited, is impregnated with a solution of sulton and heated after the excess solution has been removed. The washing is carried out after cooling as before.
As the catalyst solvent, Pmsopropanol or xylene can be used for isopropylate and potassium methoxide, and water for potassium and sodium hydroxides and for potassium acetate.
The examples below show the implementation of the process according to the above variants.
<I> Example 2 </I> A polyurethane sponge is impregnated with a 0.25% solution of potassium isopropoxide in isopropyl alcohol. The excess solution is removed and dried.
The foam is again impregnated with a solution containing 15% by weight of propane-sulfone in xylene, and the mixture is heated at 800 ° C. for one hour after having removed the excess solution. Allowed to cool and washed.
<I> Example 3 </I> The procedure is as in Example 2, but by making the first impregnation with a 0.25% solution of potassium isopropoxide -in xylene, the second with a solution of 20 % on -Weight of butane-sultone in diisobutyl ether.
<I> Example 4 </I> The procedure is as in Example 2, but making the second impregnation with a 25% solution by weight of propane-sultone in dietetic ketone: <I> Example 5 </ I > The foam is impregnated with a solution formed from 200 ml of water, 50 g of propanesultone, 4 g of potassium hydroxide and 20 ml of de @ dimethyl-form-amide. The excess solution is removed and dried.
Go heated for one hour at 800 C. Allowed to cool and washed.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1160863A CH417084A (en) | 1963-09-20 | 1963-09-20 | Process for hydrophilizing a polyurethane foam |
| FR988184A FR1409603A (en) | 1963-09-20 | 1964-09-15 | Process for hydrophilizing a polyurethane foam |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1160863A CH417084A (en) | 1963-09-20 | 1963-09-20 | Process for hydrophilizing a polyurethane foam |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH417084A true CH417084A (en) | 1966-07-15 |
Family
ID=4375111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1160863A CH417084A (en) | 1963-09-20 | 1963-09-20 | Process for hydrophilizing a polyurethane foam |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH417084A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3413245A (en) * | 1962-12-21 | 1968-11-26 | Sambeth Joerg | Process for rendering polyurethane foams hydrophilic by reacting same with a lactone |
| US3451953A (en) * | 1965-11-27 | 1969-06-24 | Elekal | Hydrophilic polyurethane foams from alcohol aldehydes |
| US3451954A (en) * | 1965-11-27 | 1969-06-24 | Elekal | Hydrophilic polyurethane foams from quaternary ammonium salts of n-disubstituted amino alcohols |
-
1963
- 1963-09-20 CH CH1160863A patent/CH417084A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3413245A (en) * | 1962-12-21 | 1968-11-26 | Sambeth Joerg | Process for rendering polyurethane foams hydrophilic by reacting same with a lactone |
| US3451953A (en) * | 1965-11-27 | 1969-06-24 | Elekal | Hydrophilic polyurethane foams from alcohol aldehydes |
| US3451954A (en) * | 1965-11-27 | 1969-06-24 | Elekal | Hydrophilic polyurethane foams from quaternary ammonium salts of n-disubstituted amino alcohols |
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