DE1183503B - Stabilization of silanes - Google Patents
Stabilization of silanesInfo
- Publication number
- DE1183503B DE1183503B DED41858A DED0041858A DE1183503B DE 1183503 B DE1183503 B DE 1183503B DE D41858 A DED41858 A DE D41858A DE D0041858 A DED0041858 A DE D0041858A DE 1183503 B DE1183503 B DE 1183503B
- Authority
- DE
- Germany
- Prior art keywords
- silanes
- stabilization
- silane
- weight
- polymerization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000004756 silanes Chemical class 0.000 title claims description 8
- 230000006641 stabilisation Effects 0.000 title claims description 5
- 238000011105 stabilization Methods 0.000 title claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 108010009736 Protein Hydrolysates Proteins 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 238000001879 gelation Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- PXPBDJVBNWDUFM-UHFFFAOYSA-N 2,3,4,6-tetranitrophenol Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O PXPBDJVBNWDUFM-UHFFFAOYSA-N 0.000 description 1
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XQDFIWLWXYFYOY-UHFFFAOYSA-N [SiH3]CCCOC(=O)C=C Chemical class [SiH3]CCCOC(=O)C=C XQDFIWLWXYFYOY-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/20—Purification, separation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESGHRIFTDESIGN SCREEN
Internat. Kl.: C07fBoarding school Class: C07f
Deutsche Kl.: 12 ο -26/03 German class: 12 ο -26/03
Nummer: 1183 503Number: 1183 503
Aktenzeichen: D 41858 IV b/12 οFile number: D 41858 IV b / 12 ο
Anmeldetag: 28. Juni 1963 Filing date: June 28, 1963
Auslegetag: 17. Dezember 1964Opening day: December 17, 1964
Nach einem älteren Vorschlag des Erfinders werden Acryloxypropylsilane als Überzugsmittel für Glasfasern verwendet, um deren Haftfestigkeit in verstärkten Kunststoffen zu verbessern. Die hiermit erzielte Haftfestigkeit ist erheblich besser als- bei Verwendung anderer Überzugsmassen für Glasfasern. Im Zuge der Entwicklung dieser Stoffe zeigten, sich indessen auf Grund der Polymerisationsneigung bei der Lagerung beträchtliche Schwierigkeiten, die-durch Zugabe der üblichen Acrylat-Polymerisationsinhibitoren, wie Hydrochinon, nicht behoben werden konnten. Diese verhindern zwar die Polymerisation nach der Zugabe, aber nur für kurze Zeit, da die Wirkung dieser Mittel stetig abnimmt, so daß nach einigen Tagen oder Wochen nur noch eine sehr geringe Inhibitorwirkung vorhanden ist. Unter diesen Bedingungen können die Produkte dann gelieren,und damit wertlos werden.According to an older proposal by the inventor, acryloxypropylsilanes are used as coating agents for Glass fibers used to reinforce their adhesive strength To improve plastics. The adhesive strength achieved in this way is considerably better than when it is used other coating compositions for glass fibers. In the course of the development of these substances, however, became apparent Considerable difficulties due to the tendency to polymerize during storage Addition of the usual acrylate polymerization inhibitors, like hydroquinone, could not be fixed. These prevent the polymerization afterwards the addition, but only for a short time, as the effect of these agents decreases steadily, so that after a few Days or weeks there is only a very low inhibitory effect. Under these conditions the products can then gel and become worthless.
Erfindungsgemäß werden nun zur Stabilisierung von Silanen der FormelAccording to the invention, the stabilization of silanes of the formula
CH2 = CRCOO(CH2)3Si(OCH3)3 CH 2 = CRCOO (CH 2 ) 3 Si (OCH 3 ) 3
worin R ein Wasserstoffatom oder einen Methylrest bedeutet, und/oder deren Hydrolysaten, diesen als Polymerisationsinhibitoren bekannte Hydroxyphenylverbindungen und 0,5 bis 10 Gewichtsprozent, bezogen auf das Gewicht der Silane, eines in Wasser und in dem Silan löslichen Alkohols zugesetzt.wherein R is a hydrogen atom or a methyl radical, and / or their hydrolysates, these as Polymerization inhibitors known hydroxyphenyl compounds and 0.5 to 10 percent by weight, based based on the weight of the silanes, an alcohol soluble in water and in the silane is added.
Vorzugsweise wird der Alkohol per se zugegeben. Er kann aber auch in situ durch Zugabe einer geringen Menge Wasser aus dem Methoxysilan gebildet werden. Hierfür können beliebige Alkohole, die sich sowohl in Wasser als auch in dem verwendeten Silan lösen, verwendet werden, z. B. Methanol, Äthanol, Propanol, Isopropanol, tert. Butanol, Äthylenglycol, Diäthylenglycol, Glyzerin, sowie Monomethyläther von Äthylenglycol, von Diäthylenglycol und von Glyzerin.The alcohol is preferably added per se. But it can also be done in situ by adding a small amount Amount of water to be formed from the methoxysilane. Any alcohols that can be used for this purpose dissolve both in water and in the silane used, can be used, e.g. B. methanol, ethanol, Propanol, isopropanol, tert. Butanol, ethylene glycol, diethylene glycol, glycerine and monomethyl ether of ethylene glycol, diethylene glycol and glycerin.
Als Polymerisationsinhibitoren können beliebige Hydroxyphenylverbindungen, die die Polymerisation von Acrylverbindungen verhindern und seit langem für die Stabilisierung monomerer organischer Acrylverbindungen üblich sind, verwendet werden. Beispiele hierfür sind Hydrochinon, Hydrochinonmonomethyläther, tert. Butylhydrochinon, Pyrogallol, tert. Butylpyrogallol, Pikrinsäure, Nitropikrinsäure, tert. Butylphenol und Hexahydrobenzol.Any hydroxyphenyl compounds which the polymerization can be used as polymerization inhibitors of acrylic compounds and has long been used for the stabilization of monomeric organic acrylic compounds are common. Examples are hydroquinone, hydroquinone monomethyl ether, tert. Butylhydroquinone, pyrogallol, tert. Butylpyrogallol, picric acid, nitropicric acid, tert. Butylphenol and hexahydrobenzene.
Im allgemeinen werden 50 bis 500 ppm (bezogen auf das Silan) der Polymerisationsinhibitoren verwendet. Die genaue Menge ist jedoch nicht entscheidend, sie muß nur für die Verhinderung der Polymerisation ausreichen.In general, 50 to 500 ppm (based on the silane) of the polymerization inhibitors are used. However, the exact amount is not critical, it only has to be used to prevent polymerization sufficient.
Stabilisierung von SilanenStabilization of silanes
Anmelder:Applicant:
Dow Corning Corporation, Midland,,Mich,,Dow Corning Corporation, Midland ,, Me ,,
(V. StA!).'.(V. StA!). '.
Vertreter:Representative:
L. F. Drissl, Rechtsanwalt, 'L. F. Drissl, lawyer, '
München 23, Clemensstr. 26Munich 23, Clemensstr. 26th
Als Erfinder benannt:Named as inventor:
John L. Speier, Midland, Mich. (V. St. A.) John L. Speier, Midland, Mich. (V. St. A.)
Beanspruchte Priorität:Claimed priority:
V. St. v. Amerika vom 2. Juli 1962 (207 029)V. St. v. America July 2, 1962 (207 029)
Durch die Zugabe des Alkohols zusammen mit dem Polymerisationsinhibitor wird die Stabilität der Silane während der Lagerung außerordentlich erhöht. Dadurch können diese weiter versandt und länger gelagert werden als bei Zugabe der Hydroxyphenylverbindung allein.Adding the alcohol together with the polymerization inhibitor increases the stability of the Silanes increased extraordinarily during storage. This allows them to be sent on and stored for longer than when adding the hydroxyphenyl compound alone.
Die Reihenfolge der Zugabe des Alkohols und des Inhibitors zu den Silanen ist' nicht entscheidend. Selbstverständlich ist es notwendig, den Inhibitor kurz nach der Herstellung des' Silans zuzufügen, da sonst die Gefahr des Gelierens besteht. Der Alkohol kann vor oder nach dem Inhibitor zugegeben werden. Es wurde gefunden, daß der Alkohol selbst dann noch die Stabilität des Systems erhöhen kann, wenn der Inhibitor bereits einen beträchtlichen Teil seiner Wirkung eingebüßt hat. Durch die erfindungsgemäße Verwendung des Alkohols kanu nicht nur die Dauer der Inhibitorwirkung verlängert werden, sondern darüber hinaus wird auch die Brauchbarkeit dieser Silane als Glasüberzugsmittel verbessert.The order in which the alcohol and the inhibitor are added to the silanes is not critical. It goes without saying that it is necessary to add the inhibitor shortly after the silane has been prepared otherwise there is a risk of gelation. The alcohol can be added before or after the inhibitor. It has been found that the alcohol can even increase the stability of the system if the inhibitor has already lost a considerable part of its effectiveness. By the invention Use of alcohol can not only extend the duration of the inhibitory effect, but also longer In addition, the usefulness of these silanes as glass coating agents is also improved.
Beispiel 1
Das Silan der Formel
CH3 example 1
The silane of the formula
CH 3
CH2 = CCOO(CH2)3Si(OCH3)3 CH 2 = CCOO (CH 2 ) 3 Si (OCH 3 ) 3
wurde mit 300 ppm Hydrochinon versetzt und die Mischung in drei Chargen aufgeteilt. Zu Charge 1 wurde kein Methanol zugegeben; Charge 2 wurde mit 1% Methanol, bezogen auf das Gewicht des300 ppm hydroquinone was added and the mixture was divided into three batches. To batch 1 no methanol was added; Charge 2 was made with 1% methanol based on the weight of the
409 758/401409 758/401
Silans, und Charge 3 mit 3 % Methanol versetzt. Alle Chargen wurden in Glasflaschen in Abwesenheit von Licht aufbewahrt. Nach einigen Tagen (Anzahl der Tage siehe folgende Tabelle) wurden jeweils Proben entnommen und auf 145° C erhitzt. Dann wurde die Zeit in Stunden registriert, bis die ersten Anzeichen einer Polymerisation sichtbar wurden und bis Gelierung eintrat. Das Erhitzen auf 145° C ist ein beschleunigtes Testverfahren und entspricht dem Stehenlassen während einiger Monate bei Raumtemperatur. Die gemachten Prozentangaben sind Gewichtsprozente. Silane, and batch 3 with 3% methanol added. All batches were in glass bottles in the absence of Light kept. After a few days (for the number of days, see the following table), samples were taken in each case removed and heated to 145 ° C. Then the time was recorded in hours until the first signs polymerisation and until gelation occurred. The heating to 145 ° C is accelerated Test procedure and corresponds to standing for a few months at room temperature. The percentages given are percentages by weight.
Beispiel 2 ao Example 2 ao
Praktisch die gleichen Ergebnisse wurden erhalten, wenn an Stelle des Silans aus Beispiel 1 das Silan der FormelPractically the same results were obtained if, instead of the silane from Example 1, the silane of the formula
verwendet wurde. Desgleichen können an Stelle des im Beispiel 1 verwendeten Methanols folgende Alkohole in den gleichen Mengenverhältnissen eingesetzt werden: Äthanol, Isopropanol, Äthylenglycol, Glyzerin sowie Monomethyläther von Äthylenglycol und von Diäthylenglycol und tertButanol.was used. Likewise, the following alcohols can be used in place of the methanol used in Example 1 The same proportions are used: ethanol, isopropanol, ethylene glycol, glycerine as well as monomethyl ether of ethylene glycol and of diethylene glycol and tert-butanol.
Claims (1)
CH8 =Stabilization of silanes of the formula
CH 8 =
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20702962A | 1962-07-02 | 1962-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1183503B true DE1183503B (en) | 1964-12-17 |
Family
ID=22768919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED41858A Pending DE1183503B (en) | 1962-07-02 | 1963-06-28 | Stabilization of silanes |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1183503B (en) |
| FR (1) | FR1360469A (en) |
| GB (1) | GB1003874A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4722807A (en) * | 1983-06-21 | 1988-02-02 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Stabilizer for acryloyloxysilane compounds |
| DE102008040475A1 (en) | 2008-07-16 | 2010-01-21 | Wacker Chemie Ag | Process for preventing the polymerization of unsaturated organosilicon compounds |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60239491A (en) * | 1984-05-15 | 1985-11-28 | Kanegafuchi Chem Ind Co Ltd | Method for stabilizing silicon-containing methacrylic acid ester |
| US11713328B2 (en) * | 2018-08-23 | 2023-08-01 | Versum Materials Us, Llc | Stable alkenyl or alkynyl-containing organosilicon precursor compositions |
| CN115038708A (en) * | 2020-02-14 | 2022-09-09 | 赢创运营有限公司 | Stabilized silane compositions |
-
1963
- 1963-06-05 FR FR936996A patent/FR1360469A/en not_active Expired
- 1963-06-20 GB GB2463963A patent/GB1003874A/en not_active Expired
- 1963-06-28 DE DED41858A patent/DE1183503B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4722807A (en) * | 1983-06-21 | 1988-02-02 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Stabilizer for acryloyloxysilane compounds |
| DE102008040475A1 (en) | 2008-07-16 | 2010-01-21 | Wacker Chemie Ag | Process for preventing the polymerization of unsaturated organosilicon compounds |
| US8247590B2 (en) | 2008-07-16 | 2012-08-21 | Wacker Chemie Ag | Method for preventing polymerization of unsaturated organosilicon compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1003874A (en) | 1965-09-08 |
| FR1360469A (en) | 1964-05-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0314966A1 (en) | Composition based on titanium chelates of diols and on titanium acylates | |
| DE935706C (en) | Method of hardening gelatin | |
| DE1175874B (en) | Stabilization of vinyl chloride polymers | |
| DE1299092B (en) | Liquid concentrates containing active oxygen with surface-active properties | |
| DE1183503B (en) | Stabilization of silanes | |
| DE1231891B (en) | Process for stabilizing polymers of monoolefinically unsaturated hydrocarbons | |
| DE1219224B (en) | Polyester molding compounds | |
| US2403794A (en) | Visible light transparent plastic | |
| DE1745919C3 (en) | Process for the production of polyurethanes | |
| DE1224488B (en) | Stabilizers for the storage stability of polyester molding compounds | |
| DE1153890C2 (en) | Softeners for cellulose derivatives | |
| EP0076471B1 (en) | Stabilisation of polyether or polyester moulding compounds against premature reaction | |
| DE1264069B (en) | Process for the production of copolymers based on styrene and acrylonitrile that are stable against the effects of light and heat | |
| DE1618935A1 (en) | N-mercaptophenyl fatty acid amides and processes for their preparation | |
| DE547987C (en) | Process for the preparation of derivatives of high molecular weight aliphatic amines | |
| DE1048028B (en) | Polymerization catalyst in solution for the production of polymers and copolymers from unsaturated organic compounds | |
| DE1299625B (en) | Process for the stabilization of tin (ó�) salts of aliphatic mono- or dicarboxylic acids | |
| DE864640C (en) | Shelf life gasoline | |
| DE2208149C3 (en) | Process for the production of polyether urethane foams | |
| DE549194C (en) | Softener for cellulose esters and ethers | |
| DE1239092B (en) | Process for the production of polyurethane foams | |
| DE1060586B (en) | Process for plasticizing cellulose derivatives | |
| DE930287C (en) | Process for the preparation of interpolymerization products | |
| DE1669965C (en) | Molecule enlargement inhibitors in hardenable mixtures of Organosihciumver compounds | |
| DE1255660B (en) | Process for the preparation of acetal peroxides containing glycol ether groups |