WO2002051879A1 - Peroxide compositions with reactive diluents - Google Patents

Peroxide compositions with reactive diluents Download PDF

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Publication number
WO2002051879A1
WO2002051879A1 PCT/NL2001/000922 NL0100922W WO02051879A1 WO 2002051879 A1 WO2002051879 A1 WO 2002051879A1 NL 0100922 W NL0100922 W NL 0100922W WO 02051879 A1 WO02051879 A1 WO 02051879A1
Authority
WO
WIPO (PCT)
Prior art keywords
peroxide
group
compound
vinyl ether
ether group
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.)
Ceased
Application number
PCT/NL2001/000922
Other languages
French (fr)
Inventor
Jan Henderikus Udding
Agnes Elisabeth Wolters
Heinz Wilhelm
Armin Pfeil
Thomas Bürgel
Lutz Sager
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hilti AG
Koninklijke DSM NV
DSM IP Assets BV
Original Assignee
Hilti AG
DSM IP Assets BV
DSM NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hilti AG, DSM IP Assets BV, DSM NV filed Critical Hilti AG
Priority to DE60120773T priority Critical patent/DE60120773T2/en
Priority to KR10-2003-7008203A priority patent/KR20040010578A/en
Priority to US10/451,049 priority patent/US7160951B2/en
Priority to JP2002552970A priority patent/JP2004516364A/en
Priority to EP01995067A priority patent/EP1358219B1/en
Publication of WO2002051879A1 publication Critical patent/WO2002051879A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C07C407/003—Separation; Purification; Stabilisation; Use of additives
    • C07C407/006—Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/28—Oxygen or compounds releasing free oxygen
    • C08F4/32—Organic compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention relates to peroxide compositions comprising a reactive diluent for the peroxide, wherein the diluent is either a component containing one or more vinyl ether group(s) and having a monomeric structure according to formula 1, (A-CH=CH-O)n-R, or is a suitable resinous compound comprising, in a covalently built-in manner, a component containing one or more vinyl ether group(s). In the formula A represents hydrogen or an alkyl group with 1-3 C atoms, and individual A groups may be different; R either represents an aliphatic group, optionally branched, with 1-20 C atoms, etc. or represents a polyethylene or polypropylene glycol with 2 to 120 glycol units, etc. and n is 1,2,3 or 4. The resinous compounds comprising, in a covalently built-in manner, a component containing one or more vinyl ether group(s) are obtained by reaction of: a) a first compound (the HVE-compound) containing at least one hydroxyl group and at least one vinyl ether group, and b) a second compound (the D/HIC-compound), being an isocyanate, reacting with formation of one or more urethane group(s), and c) a third compound (the G/P/HP-compound) chosen from the groups of (1) C2-6 glycols, (2) C5-20 polyols having 2-5 hydroxyl groups and (3) hydroxyl terminated polyester compounds, not being alkyd resins, having 1-5 free hydroxyl groups and from 2-50 monomeric ester units (the G/P/HP-compound), or mixtures thereof. The invention also relates to the preparation of such compositions and to the use of such reactive diluents for peroxides in radically curing of unsaturated polyester resins for structural applications.

Claims

- 17 -C L A I M S
1. Peroxide compositions comprising a reactive diluent for the peroxide, characterized in that the diluent is either a component containing one or more vinyl ether group(s) and having a (monomeric) structure according to formula 1
(A-CH=CH-O)n-R (formula 1)
where
A represents hydrogen or an alkyl group with 1-3 C atoms, and where, if there is more than one A, the individual A groups may be the same or different R either represents an aliphatic group, optionally branched, with 1-20 C atoms, which may also contain a cyclohexyl or a
1 ,4-dimethylenecyclohexyl group and in the carbon chain optionally also one or more O and/or S atoms, which group may be substituted with one or more functional group(s) chosen from either a hydroxyl group or an amino group, optionally substituted with one or two alkyl groups with 1-3 C atoms, or represents a polyethylene glycol or a polypropylene glycol with an average chain length of between 2 and 120 glycol units, optionally with an aliphatic group with 1-5 C atoms attached to the chain's free hydroxyl group and n is 1 , 2, 3 or 4 or is a suitable resinous compound comprising, in a covalently built-in manner, a component containing one or more vinyl ether group(s).
2. Peroxide compositions according to claim 1 , characterized in that the monomeric component containing one or more vinyl ether group(s) is selected from the group of mono- or divinyl ether monomers.
3. Peroxide compositions according to claim 2, characterized in that the component containing one or more vinyl ether group(s) is hydroxybutyl vinyl ether (HBUVE), diethyleneglycol divinyl ether (DEGDVE) or triethyleneglycol divinyl ether (TEGDVE). - 18 -
4. Peroxide compositions according to claim 1 , characterized in that the resinous compound comprising, in a covalently built-in manner, a component containing one or more vinyl ether group(s) is obtained by reaction of a mixture of appropriate amounts of: a) a first compound (the HVE-compound) containing at least one hydroxyl group and at least one vinyl ether group, and b) a second compound (the D/HIC-compound), being a diisocyanate (or higher isocyanate), reacting with formation of one or more urethane group(s), and c) a third compound (the G/P/HP-compound) chosen from the groups of (1 )
C2-6 glycols, (2) C5.20 polyols having 2-5 hydroxyl groups and (3) saturated or (ethylenically) unsaturated hydroxyl terminated polyester compounds, not being alkyd resins, having 1-5 free hydroxyl groups and from 2-50 monomeric ester units (the G/P/HP-compound), or mixtures thereof.
5. Peroxide compositions according to claim 4, characterized in that the HVE- compound is hydroxybutyl vinyl ether (HBUVE).
6. Peroxide compositions according to any of claims 4 or 5, characterized in that the resinous component carries one or more additional substituent groups for influencing the solubility of the peroxide in the peroxide composition and/or in the final application thereof.
7. Peroxide compositions according to any of claims 1 to 6, characterized in that the reactive diluent is a mixture of one or more components having one or more vinyl ether group(s).
8. Peroxide compositions according to any of claims 1 to 7, characterized in that the peroxide is selected from the group of acetylacetone peroxide, cyclohexanone peroxide, methylethylketone peroxide, dibenzoyl peroxide, alkylperoxides, hydroperoxides, percarbonates, perketals and inorganic peroxides.
9. Peroxide compositions according to claim 8, characterized in that the peroxide is acetylacetone peroxide, cyclohexanone peroxide, methylethylketone peroxide, or dibenzoyl peroxide.
10. Peroxide compositions according to any of claims 1 to 9, characterized in that the ratio between the amounts of peroxide and of diluent are chosen so that the content of peroxide in the composition is in the range of between 0.5 and 99, preferably between 1.0 and 60 wt.% of the peroxide composition. - 19 -
11. Method for preparing peroxide compositions comprising a reactive diluent for the peroxide, characterized in that an organic or inorganic peroxide is blended either with a reactive diluent selected from the group of components containing one or more vinyl ether group(s) and having a structure according to formula 1
(A-CH=CH-O)n-R (formula 1)
or is blended with a suitable resinous compound comprising, in a covalently built-in manner, a component containing one or more vinyl ether group(s) as is obtained by reaction of a mixture of appropriate amounts of a), b) and c) as indicated in claim 4.
12. Use of a reactive diluent containing peroxide composition according to one of claims 1-10 or prepared according to claim 11 in processes for curing of radically curable resins.
13. Products obtained by curing with a peroxide composition according to one of claims 1-10 or prepared according to claim 11.
PCT/NL2001/000922 2000-12-22 2001-12-19 Peroxide compositions with reactive diluents Ceased WO2002051879A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DE60120773T DE60120773T2 (en) 2000-12-22 2001-12-19 PEROXIDE COMPOSITIONS WITH REACTIVE DILUENTS
KR10-2003-7008203A KR20040010578A (en) 2000-12-22 2001-12-19 Peroxide compositions with reactive diluents
US10/451,049 US7160951B2 (en) 2000-12-22 2001-12-19 Peroxide compositions with reactive diluents
JP2002552970A JP2004516364A (en) 2000-12-22 2001-12-19 Peroxide composition containing reactive diluent
EP01995067A EP1358219B1 (en) 2000-12-22 2001-12-19 Peroxide compositions with reactive diluents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP00204745.4 2000-12-22
EP00204745A EP1221449A1 (en) 2000-12-22 2000-12-22 Peroxide compositions with reactive diluents

Publications (1)

Publication Number Publication Date
WO2002051879A1 true WO2002051879A1 (en) 2002-07-04

Family

ID=8172523

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL2001/000922 Ceased WO2002051879A1 (en) 2000-12-22 2001-12-19 Peroxide compositions with reactive diluents

Country Status (9)

Country Link
US (1) US7160951B2 (en)
EP (2) EP1221449A1 (en)
JP (1) JP2004516364A (en)
KR (1) KR20040010578A (en)
CN (1) CN1274720C (en)
AT (1) ATE329934T1 (en)
DE (1) DE60120773T2 (en)
WO (1) WO2002051879A1 (en)
ZA (1) ZA200304681B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6893584B2 (en) 2003-04-25 2005-05-17 Crompton Corporation Stabilized organic peroxide composition and process for making the same
EP2532632A2 (en) 2011-06-09 2012-12-12 HILTI Aktiengesellschaft Inhibitor combination, resin mixture containing same and use of same
EP2532636A2 (en) 2011-06-09 2012-12-12 HILTI Aktiengesellschaft Inhibitor, resin mixture containing same and use of same

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1217017A1 (en) * 2000-12-22 2002-06-26 Dsm N.V. Resin mortars for chemical fastening
EP1221449A1 (en) 2000-12-22 2002-07-10 Dsm N.V. Peroxide compositions with reactive diluents
EP1513805A1 (en) * 2002-06-20 2005-03-16 Akzo Nobel N.V. (stabilised) peroxide compositions phlegmatised with a specific unsaturated phlegmatising agent
KR100972276B1 (en) * 2007-09-27 2010-07-23 서인원 Cap of drink bottle
US9109107B2 (en) 2007-12-06 2015-08-18 Dsm Ip Assets B.V. Peroxide composition
AU2011206922A1 (en) * 2010-01-13 2012-07-26 University Of Wollongong Curable composition
DK2906947T3 (en) * 2013-03-07 2017-03-06 Rapid Pathogen Screening Inc Multiplanart lateral flow assay with redirect zone
FR3121682A1 (en) * 2021-04-07 2022-10-14 Arkema France Composition comprising at least one aromatic peroxide and at least one compound having an ether group
US20240182605A1 (en) * 2021-04-07 2024-06-06 Arkema France Composition comprising at least one aromatic peroxide and at least hydrogen peroxide

Citations (3)

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Publication number Priority date Publication date Assignee Title
GB915009A (en) * 1958-05-31 1963-01-09 Hoechst Ag Process for the manufacture of explosion-proof peroxide solutions
US4130501A (en) * 1976-09-20 1978-12-19 Fmc Corporation Stable viscous hydrogen peroxide solutions containing a surfactant and a method of preparing the same
WO2000009478A1 (en) * 1998-08-12 2000-02-24 Akzo Nobel N.V. Peroxides, their preparation process and use

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US3876726A (en) * 1973-05-29 1975-04-08 Ici America Inc Vinyl ester urethanes
US4100225A (en) * 1974-06-20 1978-07-11 Ciba-Geigy Corporation Stable polymer compositions containing perfluoroalkyl groups and process for making
US4374215A (en) 1979-11-13 1983-02-15 Union Carbide Corporation Polyester moldings
DE3226602A1 (en) 1982-07-16 1984-01-19 Hilti AG, 9494 Schaan HARDENABLE RESIN MATERIALS AND THEIR USE
JPS59152914A (en) * 1983-02-18 1984-08-31 Asahi Glass Co Ltd Curable resin composition
MX169697B (en) * 1987-12-28 1993-07-19 Ppg Industries Inc IMPROVEMENTS TO RADIATION-FRAGABLE COMPOSITIONS BASED ON UNSATURATED POLYESTERS AND COMPOUNDS HAVING AT LEAST TWO GROUPS OF VINYL ETER
DE3812814A1 (en) * 1988-04-16 1989-11-02 Hilti Ag USE OF TWO-COMPONENT REACTION RESIN FOR FASTENING PURPOSES
DE3940138A1 (en) * 1989-12-05 1991-06-06 Hilti Ag USE OF HAERTBAR CYCLOALIPHATE DERIVATIVES IN DUPLICATE
DE3940309A1 (en) 1989-12-06 1991-06-13 Hilti Ag MOERTELMASSE
DE4131457A1 (en) 1991-09-21 1993-03-25 Basf Ag CARTRIDGE OR CARTRIDGE FOR CHEMICAL FASTENING TECHNOLOGY
DE4131458A1 (en) 1991-09-21 1993-03-25 Basf Ag TWO-COMPONENT ADHESIVE MATERIAL FOR CHEMICAL FIXING TECHNOLOGY
DE4231161A1 (en) 1992-09-17 1994-03-24 Hilti Ag Mortar and device for fixing anchoring means in boreholes
DE4233429A1 (en) 1992-10-05 1994-04-07 Basf Ag Cartridge or cartridge for chemical fastening technology
DE4304824A1 (en) 1993-02-17 1994-08-18 Upat Max Langensiepen Kg Reaction resin mortar for two-component systems
DE4314866A1 (en) * 1993-05-05 1994-11-10 Bayer Ag Radically curable lacquer composition and its use as furniture lacquer
JP2707230B2 (en) 1995-08-21 1998-01-28 日本合成化学工業株式会社 Curable resin composition
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NL1012418C2 (en) 1999-06-23 2000-12-28 Dsm Nv Vinyl ethers in unsaturated polyester resins, vinyl esters and vinyl ester urethanes for construction applications.
EP1221449A1 (en) 2000-12-22 2002-07-10 Dsm N.V. Peroxide compositions with reactive diluents
EP1225189A1 (en) * 2000-12-22 2002-07-24 Dsm N.V. Two-component chemical fastening systems
EP1217017A1 (en) * 2000-12-22 2002-06-26 Dsm N.V. Resin mortars for chemical fastening

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB915009A (en) * 1958-05-31 1963-01-09 Hoechst Ag Process for the manufacture of explosion-proof peroxide solutions
US4130501A (en) * 1976-09-20 1978-12-19 Fmc Corporation Stable viscous hydrogen peroxide solutions containing a surfactant and a method of preparing the same
WO2000009478A1 (en) * 1998-08-12 2000-02-24 Akzo Nobel N.V. Peroxides, their preparation process and use

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6893584B2 (en) 2003-04-25 2005-05-17 Crompton Corporation Stabilized organic peroxide composition and process for making the same
EP2532632A2 (en) 2011-06-09 2012-12-12 HILTI Aktiengesellschaft Inhibitor combination, resin mixture containing same and use of same
EP2532636A2 (en) 2011-06-09 2012-12-12 HILTI Aktiengesellschaft Inhibitor, resin mixture containing same and use of same
US8440278B2 (en) 2011-06-09 2013-05-14 Hilti Aktiengesellschaft Inhibitor, resin mixture containing same and use of same
US8735475B2 (en) 2011-06-09 2014-05-27 Hilti Aktiengesellschaft Inhibitor combination, resin mixture containing same and use of same

Also Published As

Publication number Publication date
DE60120773D1 (en) 2006-07-27
ZA200304681B (en) 2004-07-26
ATE329934T1 (en) 2006-07-15
CN1274720C (en) 2006-09-13
US7160951B2 (en) 2007-01-09
EP1358219A1 (en) 2003-11-05
DE60120773T2 (en) 2007-02-08
EP1358219B1 (en) 2006-06-14
KR20040010578A (en) 2004-01-31
EP1221449A1 (en) 2002-07-10
US20040094744A1 (en) 2004-05-20
CN1483044A (en) 2004-03-17
JP2004516364A (en) 2004-06-03

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