WO1995030480A3 - Initiators of tertiary amine/peroxide and polymer - Google Patents

Initiators of tertiary amine/peroxide and polymer Download PDF

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Publication number
WO1995030480A3
WO1995030480A3 PCT/US1995/005406 US9505406W WO9530480A3 WO 1995030480 A3 WO1995030480 A3 WO 1995030480A3 US 9505406 W US9505406 W US 9505406W WO 9530480 A3 WO9530480 A3 WO 9530480A3
Authority
WO
WIPO (PCT)
Prior art keywords
peroxide
amine
employed
dmpt
initiators
Prior art date
Application number
PCT/US1995/005406
Other languages
French (fr)
Other versions
WO1995030480A2 (en
Inventor
Drahoslav Lim
David Arthur Gough
Andrea M Rourke
Original Assignee
Univ California
Drahoslav Lim
David Arthur Gough
Andrea M Rourke
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 Univ California, Drahoslav Lim, David Arthur Gough, Andrea M Rourke filed Critical Univ California
Priority to JP7529036A priority Critical patent/JPH10500154A/en
Priority to EP95917785A priority patent/EP0758268A4/en
Priority to AU23718/95A priority patent/AU2371895A/en
Publication of WO1995030480A2 publication Critical patent/WO1995030480A2/en
Publication of WO1995030480A3 publication Critical patent/WO1995030480A3/en

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0209—Esters of carboxylic or carbonic acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • 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
    • C08F4/34—Per-compounds with one peroxy-radical
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
    • B01J2231/12—Olefin polymerisation or copolymerisation
    • B01J2231/125—Radical (co)polymerisation, e.g. mediators therefor

Abstract

Cement compositions used in biomedical applications including initiation systems containing at least one peroxide or amine which has a higher molecular weight than the employed peroxide BPO and amine DMpT, respectively. Derivatives of peroxides and amines bearing large substitutents relative to BPO and DMpT and polymeric peroxides and amines are suitably employed in the reaction mixture. Through the use of these initiator systems in which one or more of the components has reduced mobility relative to the materials employed in the conventional mixtures, it is possible to control the exothermicity and the peak temperature of the polymerization of the material. The choice of components for use in the initiation system advantageously results in a reduction in the generation of waste products and in the potential toxicity of the composition. Initiators having structures with substituents attached to the benzoyl peroxide or the amine skeleton and equivalent to at least about 4 additional carbon atoms are preferred. Porosity and shrinkage of cement products are addressed through selection of appropriate comonomers for use with or in place of methyl methacrylate. Hydrophilic comonomers and/or monomers with lower vapor tension than methyl methacrylate are preferred for this purpose.
PCT/US1995/005406 1994-05-02 1995-05-02 Initiators of tertiary amine/peroxide and polymer WO1995030480A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP7529036A JPH10500154A (en) 1994-05-02 1995-05-02 Polymer cement composition and initiator for its production
EP95917785A EP0758268A4 (en) 1994-05-02 1995-05-02 Polymer cement compositions and initiators for use in the preparation thereof
AU23718/95A AU2371895A (en) 1994-05-02 1995-05-02 Polymer cement compositions and initiators for use in the preparation thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US23697494A 1994-05-02 1994-05-02
US08/236,974 1994-05-02

Publications (2)

Publication Number Publication Date
WO1995030480A2 WO1995030480A2 (en) 1995-11-16
WO1995030480A3 true WO1995030480A3 (en) 1995-12-21

Family

ID=22891797

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/005406 WO1995030480A2 (en) 1994-05-02 1995-05-02 Initiators of tertiary amine/peroxide and polymer

Country Status (5)

Country Link
US (1) US6348429B1 (en)
EP (1) EP0758268A4 (en)
JP (1) JPH10500154A (en)
AU (1) AU2371895A (en)
WO (1) WO1995030480A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001074301A1 (en) 2000-04-03 2001-10-11 3M Innovative Properties Company Dental materials with extendable work time, kits, and methods
FR2838334B1 (en) * 2002-04-16 2006-05-26 Polymerexpert Sa NON-TOXIC RADICAL POLYMERIZATION ACTIVATOR FOR BONE OR DENTAL CEMENT
AU2008274369A1 (en) * 2007-07-12 2009-01-15 Evonik Rohm Gmbh Two or more-component system cured by a redox initiator system with controllable working life, and the use thereof
JP2010532811A (en) * 2007-07-12 2010-10-14 エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング Emulsion polymers containing active agents, processes for their preparation, and their use in two-component or multicomponent systems
BR112016008070B8 (en) 2013-10-17 2022-08-23 Dow Agrosciences Llc PESTICIDE COMPOUNDS AND THEIR PREPARATION PROCESSES
CN110325036B (en) 2016-12-29 2021-10-26 美国陶氏益农公司 Process for preparing pesticidal compounds
TW201823201A (en) * 2016-12-29 2018-07-01 美商陶氏農業科學公司 Processes for the preparation of pesticidal compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4093573A (en) * 1974-04-29 1978-06-06 Basf Wyandotte Corporation Low-viscous, stable polymer dispersions and polyurethanes prepared therefrom
US4299942A (en) * 1978-11-06 1981-11-10 Usm Corporation Adhesive composition
US4404237A (en) * 1980-12-29 1983-09-13 General Electric Company Fabrication of electrical conductor by replacement of metallic powder in polymer with more noble metal

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE540292A (en) * 1954-08-04
CH564340A5 (en) * 1972-06-12 1975-07-31 Sulzer Ag
DE2303314C3 (en) * 1973-01-24 1980-11-06 Roehm Gmbh, 6100 Darmstadt Use of tertiary amines, which have been prepared by the addition of NJN-diethanol-p-toluidine or N, N-diisopropanol-p-toluidine onto isophorone diisocyanate, p-toluenesulfonyl monoisocyanate or 4,4-diphenylmethane diisocyanate, as a reducing component of a redox system for the Polymerization of vinyl and (meth) acrylic monomers
CH618188A5 (en) * 1975-12-24 1980-07-15 Espe Pharm Praep
US4156766A (en) * 1977-01-10 1979-05-29 Johnson & Johnson Acrylic polymerization systems and diacyl peroxide catalysts therefor
US4243763A (en) * 1978-03-10 1981-01-06 American Dental Association Health Foundation Tertiary aromatic amine accelerators in acrylic resin
DE2913220A1 (en) * 1979-04-03 1980-10-23 Bayer Ag COLD-HARDENING MATERIAL
US4284551A (en) * 1979-11-30 1981-08-18 American Dental Association Health Foundation Tertiary aromatic amine accelerators derived from para-aminophenethanol
CA1233831A (en) * 1983-04-26 1988-03-08 Louis H. Tateosian Organic amine salt of an acid, manufacture and use as accelerator
US4670480A (en) * 1985-08-16 1987-06-02 Morrone Rudolph D Dental prosthesis composition
US4910259A (en) * 1988-09-26 1990-03-20 Wolff & Kaaber A/S Bone cement

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4093573A (en) * 1974-04-29 1978-06-06 Basf Wyandotte Corporation Low-viscous, stable polymer dispersions and polyurethanes prepared therefrom
US4299942A (en) * 1978-11-06 1981-11-10 Usm Corporation Adhesive composition
US4404237A (en) * 1980-12-29 1983-09-13 General Electric Company Fabrication of electrical conductor by replacement of metallic powder in polymer with more noble metal

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
AKTUELLE PROBLEME CHIR. ORTHOP., Volume 31, issued 1987, H. SEIDEL et al., "Neuentwicklung Eines Quellbaren Knochenzementes", pages 354-357. *
ANN. CHEMIE, Volume 573, issued 1951, VON L. HORNER et al., "Der Serfall von Dibenzoylperoxyd Durch Substituierte Tertiare Amine", pages 35-55. *
CLINICAL ORTHOPEDICS, Volume 225, issued December 1987, JONES et al., "Cement Disease", pages 192-206. *
JOURNAL OF BIOMEDICAL MATERIALS RESEARCH, Vol. 20, issued 1986, G.M. BRAUER et al., "Dependence of Curing Time, Peak Temperature and Mechanical Properties on the Composition of Bone Cement", pages 839-852. *
JOURNAL OF DENT. RES., Volume 60, Number 7, issued July 1981, G.M. BRAUER et al., "4-N, N-Dialkylamino- Phenethanols,- Alkanoic Acids and Esters: New Accelerators for Dental Composites", pages 1343-1348. *
See also references of EP0758268A4 *
The 13th Annual Meeting of the Society for Biomaterials, issued June 1987, CONNELLY et al., "The Role of Porosity in the Shrinkage of Acrylic Bone Cement", page 114. *

Also Published As

Publication number Publication date
WO1995030480A2 (en) 1995-11-16
EP0758268A1 (en) 1997-02-19
AU2371895A (en) 1995-11-29
JPH10500154A (en) 1998-01-06
US6348429B1 (en) 2002-02-19
EP0758268A4 (en) 1999-04-28

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