GB1111603A - Creation of Inventions and Patents with Artificial Intelligence

GB1111603A – Reinforced poly(alkyl methacrylate) compositions
– Google Patents

GB1111603A – Reinforced poly(alkyl methacrylate) compositions
– Google Patents
Reinforced poly(alkyl methacrylate) compositions

Info

Publication number
GB1111603A

GB1111603A
GB652/66A
GB65266A
GB1111603A
GB 1111603 A
GB1111603 A
GB 1111603A
GB 652/66 A
GB652/66 A
GB 652/66A
GB 65266 A
GB65266 A
GB 65266A
GB 1111603 A
GB1111603 A
GB 1111603A
Authority
GB
United Kingdom
Prior art keywords
alkyl
reinforcing
methacrylate
agents
reacting
Prior art date
1965-01-06
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.)

Expired

Application number
GB652/66A
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.)

Monsanto Co

Original Assignee
Monsanto Co
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.)
1965-01-06
Filing date
1966-01-06
Publication date
1968-05-01

1966-01-06
Application filed by Monsanto Co
filed
Critical
Monsanto Co

1968-05-01
Publication of GB1111603A
publication
Critical
patent/GB1111603A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

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

C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials

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 System

C07F7/02—Silicon compounds

C07F7/08—Compounds having one or more C—Si linkages

C07F7/12—Organo silicon halides

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 System

C07F7/02—Silicon compounds

C07F7/08—Compounds having one or more C—Si linkages

C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages

C07F7/1804—Compounds having Si-O-C linkages

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 System

C07F7/02—Silicon compounds

C07F7/08—Compounds having one or more C—Si linkages

C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages

C07F7/1896—Compounds having one or more Si-O-acyl linkages

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

C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System

C07F9/66—Arsenic 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

C08F2/00—Processes of polymerisation

C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers

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

C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof

C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof

C08F20/10—Esters

C08F20/12—Esters of monohydric alcohols or phenols

Abstract

Reinforced polymeric compositions comprise an alkyl methacrylate polymer, an inorganic reinforcing agent (having a solubility in water of less than 0.15 g/l. and having, or acquiring on treatment with a base, an alkaline surface), and residues, derived from a coupling agent, linking polymer molecules to the reinforcing agent, said coupling agent being of the formula where R is H or alkyl, X is a hydrolysable radical (e.g. halogen or an alkyl carboxylate, alkoxycarbonyl, alkoxy or hydroxy group), Y is a hydrocarbon group, Z is C7-C20 alkylene, a is 1, 2 or 3, b is 0, 1 or 2, c is 1, 2 or 3, and a + b + c = 4. The compositions are prepared by polymerizing an alkyl methacrylate in the presence of the reinforcing and coupling agents; the latter two agents may first be pre-reacted to form a so-called “adduct”. The alkyl methacrylate may be homopolymerized, or copolymerized with other alkyl methacrylates or with different comonomers, e.g. alkyl acrylates, styrene and its derivatives, acrylonitrile, methacrylonitrile, hydroxyalkyl methacrylates, maleic anhydride, biallyl, dimethacrylates and trimethacrylates. Specified reinforcing agents are alumina, feldspar, wollastonite, asbestos, crocidolite, quartz, silica gel, ground glass, glass fibres, cristobalite, various metals of Groups II to VIII and oxides thereof, heavy metal phosphates, sulphides and sulphates in gel form, spodumene, mullite, mica, montmorillonite, kaolinite, bentonite, hectorite, beidellite, attapulgite, graphite, chrysolite, garnet, saponite and hercynite. The viscosity of the polymerizable mixture can be reduced, if necessary, by adding a surface-active agent, e.g. zinc stearate, long chain alkyl trimethyl ammonium halides and alkylene oxide condensates of long chain carbon compounds. The pre-reacted “adduct” can be obtained by bringing the coupling and reinforcing agents together, preferably at 40-150 DEG C., in an inert liquid dispersion medium, e.g. water, alcohol or dioxan, which product is then preferably dried before being used in the polymerization mixture; alternatively, said agents may be prereacted in the monomer, and the mixture dried to remove volatile reaction products. The polymerization is initiated by means of a free-radical catalyst, of which many examples are listed, preferably a peroxy compound; an activator may also be used, e.g. a boron hydride or borane (optionally complexed with various basic compounds, such as amines or triphenylphosphine, or with tetrahydrofuran) or a redox reducing component. The polymerization is generally effected using a casting process so as to obtain shaped products. The coupling agents of the above formula wherein X represents a hydroxy, hydrocarbyloxy or alkyl carboxylate group can be prepared by reacting a compound R1OH (where R1 is H, hydrocarbyl or alkyl carbonyl) with a halosilyalkyl alkanoate of the formula where X1 is halogen and Alk is alkyl, and then reacting the product with (alk)acrylic acid or an ester thereof. The halosilyl compound can itself be obtained by reacting an alkenyl alkanoate with an appropriate halogenated silane, preferably in the presence of a catalyst consisting of or containing a metal of the platinum or palladium series. The coupling agents can also be used in reinforcing other polymer systems, e.g. polystyrenes, polyesters, acrylonitrile-butadiene-styrene copolymers and styrene-acrylonitrile copolymers. They are also suitable for rendering hydrophilic substances water-repellant and for use as monomers in the preparation of polysiloxane resins. Examples illustrate the polymerization of methyl methacrylate using benzoyl peroxide catalyst and of ethyl methacrylate using a cumene hydro-peroxide-triethylborane-pyridine catalyst system dissolved in an onyl phenol-ethylene oxide condensate; using a reinforcing adduct of wollastonite / 11 – trimethoxysilylundecyl methacrylate, feldspar / 18 – trichlorosilyloctadecyl acrylate or wollastonite/18-acrylato-octadecyl-triacetoxysilane. Examples also illustrate the preparation of 11 – (trimethoxysilyl)undecyl methacrylate by reacting undecenyl acetate with trichlorosilane in the presence of chloroplatinic acid to form trichlorosilylundecyl acetate which is then reacted with methacrylic acid to give the desired compound; and the analogous preparation of 18-acrylato-octadecyl triacetoxysilane starting from 17-octadecenyl propionate.

GB652/66A
1965-01-06
1966-01-06
Reinforced poly(alkyl methacrylate) compositions

Expired

GB1111603A
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

US42384265A

1965-01-06
1965-01-06

US44578165A

1965-04-05
1965-04-05

Publications (1)

Publication Number
Publication Date

GB1111603A
true

GB1111603A
(en)

1968-05-01

Family
ID=27026160
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB652/66A
Expired

GB1111603A
(en)

1965-01-06
1966-01-06
Reinforced poly(alkyl methacrylate) compositions

Country Status (9)

Country
Link

US
(1)

US3427337A
(en)

AT
(2)

AT281412B
(en)

BE
(1)

BE674610A
(en)

DE
(1)

DE1694574A1
(en)

GB
(1)

GB1111603A
(en)

IL
(1)

IL24917A
(en)

LU
(1)

LU50213A1
(en)

NL
(1)

NL6600164A
(en)

SE
(1)

SE334471B
(en)

Cited By (6)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

FR2576309A1
(en)

1984-12-05
1986-07-25
Gen Electric

PROCESS FOR MANUFACTURING ACRYLIC FUNCTIONALITY SILICON COMPOSITIONS

EP0368657A2
(en)

1988-11-11
1990-05-16
Kuraray Co., Ltd.
Dental restorative material

US5385973A
(en)

1987-12-17
1995-01-31
Vedril S.P.A.
Process for preparing flowable, stable and hardenable suspensions, and thus-obtained compositions

EP2993200A1
(en)

2014-09-02
2016-03-09
Greenseal Chemicals NV
Thiol-acrylate based foam precursor composition

WO2017036525A1
(en)

2015-09-02
2017-03-09
Greenseal Chemicals Nv
Thiol-acrylate based foam precursor composition

WO2022029237A1
(en)

2020-08-05
2022-02-10
Greenseal Nv
Method for obtaining an oxygen curable composition using a borane compound as oxygen scavenger

Families Citing this family (14)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3700714A
(en)

1971-06-24
1972-10-24
Stephen B Hamilton
Curable compositions

DE2655877A1
(en)

1976-12-09
1978-06-15
Wacker Chemie Gmbh

PROCESS FOR MANUFACTURING AND USING SILANES

JPS6017799B2
(en)

1979-06-29
1985-05-07
信越化学工業株式会社

organosilicon compounds

US4281145A
(en)

1980-04-02
1981-07-28
General Electric Company
Process for producing alkoxylated silanes

GB8405731D0
(en)

1984-03-05
1984-04-11
Dow Corning Ltd
Preparation of organosiloxanes

US4659851A
(en)

1986-03-26
1987-04-21
Dow Corning Corporation
Novel organosilicon compounds

JPS63179881A
(en)

1987-01-19
1988-07-23
Shin Etsu Chem Co Ltd
Organosilicon compound

US5391677A
(en)

1991-07-23
1995-02-21
Shin-Etsu Chemical Co., Ltd.
Acrylic-functional organopolysiloxane and method for the preparation thereof

DE4225309A1
(en)

1992-07-31
1994-02-03
Roehm Gmbh

Suspension for the production of filled casting resins

JP5631547B2
(en)

2007-02-01
2014-11-26
クラレノリタケデンタル株式会社

Dental curable composition

CN105152237A
(en)

2015-08-30
2015-12-16
常州市鼎日环保科技有限公司
Method for manufacturing attapulgite-based porous super-hydrophobicity materials

DE102016105525A1
(en)

2016-03-24
2017-09-28
Blanco Gmbh + Co Kg

Curable casting compound for the production of plastic moldings and their use

CN112385562A
(en)

2020-11-09
2021-02-23
黄高卫
Clothes for pet dog

CN115043591B
(en)

2022-07-20
2023-05-12
西南科技大学
Porous microcrystalline ceramic and preparation method thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3317369A
(en)

1961-04-07
1967-05-02
Dow Corning
Acryloxyalkylsilane compositions and the fabrication of structures therewith

US3227675A
(en)

1963-05-01
1966-01-04
Huber Corp J M
Silane-treated clay reinforced resin compositions

1965

1965-04-05
US
US445781A
patent/US3427337A/en
not_active
Expired – Lifetime

1965-12-30
SE
SE17011/65A
patent/SE334471B/xx
unknown

1965-12-31
BE
BE674610D
patent/BE674610A/xx
unknown

1966

1966-01-04
IL
IL24917A
patent/IL24917A/en
unknown

1966-01-05
DE
DE19661694574
patent/DE1694574A1/en
active
Pending

1966-01-06
LU
LU50213A
patent/LU50213A1/xx
unknown

1966-01-06
NL
NL6600164A
patent/NL6600164A/xx
unknown

1966-01-06
GB
GB652/66A
patent/GB1111603A/en
not_active
Expired

1966-01-07
AT
AT12366A
patent/AT281412B/en
not_active
IP Right Cessation

1966-01-07
AT
AT03822/69A
patent/AT285628B/en
not_active
IP Right Cessation

Cited By (8)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

FR2576309A1
(en)

1984-12-05
1986-07-25
Gen Electric

PROCESS FOR MANUFACTURING ACRYLIC FUNCTIONALITY SILICON COMPOSITIONS

US5385973A
(en)

1987-12-17
1995-01-31
Vedril S.P.A.
Process for preparing flowable, stable and hardenable suspensions, and thus-obtained compositions

EP0368657A2
(en)

1988-11-11
1990-05-16
Kuraray Co., Ltd.
Dental restorative material

EP0368657A3
(en)

1988-11-11
1991-04-03
Kuraray Co., Ltd.
Dental restorative material

EP2993200A1
(en)

2014-09-02
2016-03-09
Greenseal Chemicals NV
Thiol-acrylate based foam precursor composition

WO2017036525A1
(en)

2015-09-02
2017-03-09
Greenseal Chemicals Nv
Thiol-acrylate based foam precursor composition

US10875942B2
(en)

2015-09-02
2020-12-29
Greenseal Nv
Thiol-acrylate based foam precursor composition

WO2022029237A1
(en)

2020-08-05
2022-02-10
Greenseal Nv
Method for obtaining an oxygen curable composition using a borane compound as oxygen scavenger

Also Published As

Publication number
Publication date

BE674610A
(en)

1966-06-30

AT281412B
(en)

1970-05-25

NL6600164A
(en)

1966-07-07

SE334471B
(en)

1971-04-26

US3427337A
(en)

1969-02-11

AT285628B
(en)

1970-11-10

IL24917A
(en)

1969-11-30

DE1694574A1
(en)

1972-03-16

LU50213A1
(en)

1966-07-06

Contact information