Chloroethyl formal, bis

Synonyms AI3-01455 BCEXM Bis(2-chloroethyl)formal Bis(P-chloroethyl)formal BRN 1698909 Dichlorodiethyl formal Dichlorodiethyl methylal Dichloroethyl formal Di-2-chloro-ethyl acetal Di-2-chloroethyl formal 2,2-Dichloroethyl formal EINECS 203-920-2 l,l -[Meth-ylenebis(oxy)]bis(2-chloroethane) l,l -[Methylenebis(oxy)]bis(2-chloroformaldehyde) Bis(p-chloroethyl)acetal ethane Formaldehyde bis(p-chloroethylacetal) NSC 5212 RCRA waste number U024 UN 1916. 

Most of the polysulfide polymers are made from bis(2-chloroethyl)formal [bis(2-chloroethoxy)methane], which is... 

Beilstein Handbook Reference) AI3-01455 Bis (5-chloroethyl) formal Bis(2-chloro-elhoxy)-methane BRN 1698909 Lflchlorodiethyl formal Dichlorodiethyl methylal Dichloromethoxy ethane EINECS 203-920-2 Ethane, 1,1 -(methylenebis(oxy))bis(2-chloro- Fomnakfehyde bis(2-chloroethyl) acetal HSDB 1333 Methane, bis(2-chloroethoxy)- NSC 5212 RCRA waste number U024. 

Synonyms Bis (2-chloroethyl) formal Bis (P-chloroethyl) formal Dichlorodiethyl formal Dichloroethyl formal Ethane, 1,1-(methylenebis (oxy) bis (2-chloro-Formaldehyde, bis (2-chloroethyl) acetal Formaldehyde bis (P-chloroethyl) acetal 1,1 -[Methylene bis (oxy)] bis (2-chloroethane) Empirical C5H10CI2O2... 

Bis (2-chloroethyl) ether Bis (P-chloroethyl) ether. See sym-Dichloroethyl ether Bis (2-chloroethyl) formal Bis (P-chloroethyl) formal. See Bis (2-chloroethoxy) methane Bis (2-chloroethyl) vinylphosphonate. See Bis (P-chloroethyl) vinyl phosphonate Bis (P-chloroethyl) vinyl phosphonate CAS 115-98-0... 

Bis(p-chloroethyl) ether, see Bis(2-chloroethyl) ether Bis(2-chloroethyl)formal, see Bis(2-chloroethoxy)methane Bis(p-chloroethyl)formal, see Bis(2-chloroethoxy)methane Bis(p-chloroisopropyl) ether, see Bis(2-chloroisopropyl) ether... 

Ethylene chlorohydrin is made from HCl and ethylene epoxide. When small amounts of 1,2,3-trichloropropane are added to the bis(2-chloroethyl)formal, some branching of the otherwise linear polymer structure is achieved. 

The polymer is then in a stripped state in which no polysulfane group exceeds the disulfane stage. Thiokol FA is a copolymer of dichloroethane and the bis(2-chloroethyl)formal sodium polysulfide reaction product. 

SYNS BIS(2-CHLOROETHOXY)METHANE BIS(2-CHLOROETHYL)FORMAL DICHLOROETHYL FORMAL DI-2-CHLOROETHYL FORMAL Q FORMALDEHYDE BIS(P CHLOROETHYL) ACETAL l,l -(METHYLENEBIS(OXY)BIS(2-CHLOROETHi NE)) RCRA WASTE NUMBER U024... 

Synonym bis( 3-chloroethyl)formal, (3, 3-dichlorodiethyl formal, dichlorodiethyl methylal Chemical Name bis(2-chloroethoxy)methane CAS Registry No 111-91-1... 

The use of bis (2-chloroethyl) formal as the predominant monomer in the manufacture of polysulphides results in the formation of polymers with very good low-temperature properties. The glass transition temperature of these disulphide polymers is -59°C. Furthermore, there is no tendency in these polymers to crystallise at a temperature above the glass transition point. A glass transition temperature of -59°C applies to all the commercial liquid polysulphide (LP) polymers. 

In the case of polymers based on bis(2-chloroethyl) formal the thermally decomposed polymers exhibit a plastic-like, brittle, non-elastomeric consistency which is due to the formation of the cyclic crystalline compound dithiane (Berenbaum, 1969) ... 

Rosenthal, N.A. and Berenbaum, M.B. (1957) Thermal decomposition of bis (2-chloroethyl formal). Paper presented at the 131st Meeting of the American Chemical Society, Miami, FL, April 7-12. 

SYNONYMS dichloroethyl formal, dichlorodiethyl formal, bis (beta-chloroethyl) formal, formaldehyde bis (beta-chloroethyl) acetal, dichlorodiethyl methylal, BCEXM... 

For polysulfides at 176°F (SO C) the relaxation constant is shown for different curative systems. (See Table II). This ability of polysulfides to relieve stress is valuable in maintaining adhesion in joints where movement must be accommodated. Polysulfide polymers which are based on bis chloroethyl formal show no evidence of crystallization at low temperatures and have a glass transition temperature of -74°F (-59 C). 

Polysulfide rubber manufacturing processes are described in more detail by Bertozzi [26]. Briefly, the processes involve preparation of sodium polysulfide (S + NaOH), and reaction with bis(2-chloroethyl)formal along with 2% of a branching agent such as 1,2,3-trichloropropane to give a mercaptan terminated polymer of MW approximately 80,000 similar to that described in Preparation 2-2, Method A. 

Polysulfide elastomers are produced by the reaction of an aliphatic dihalide, usually bis(2-chloroethyl)formal, with sodium polysulfide under alkaline conditions ... 

Bis(2-chloroethyl)-formal, (C1CH2CH20)2CH2, is the halogen compound most often used industrially, and this leads to a sulfur grade of 2. 1,2-Dichloroethane is also used in some cases, and this gives a sulfur grade of 4, and in other cases, a mixture of bis(2-chloroethyl)-formal and 1,2-dichloro-ethane is used (sulfur grade 2.2). 

Ethylene dichloride, bis-(jS-chloroethoxy)-methane [bis(2-chloroethyl)-for-mal], bis(2-chloroethyl)-ether, and allyl or benzyl halides are suitable halogen compounds nowadays, mainly bis(2-chloroethyl)-formal is used commercially. Aromatic halogen compounds or vinyl halides are too reactive. The rate of the condensation reaction is increased by ionizing solvents or elevated temperatures. It is not necessary to add the two reaction components in equivalent quantities. In fact, excess Na2S causes —SNa— end groups to be formed these end groups can then undergo a disproportionation reaction ... 

Polyester and polyamide hot melt adhesives are made by step polymerization. Polysulfide sealants are made by reaction of sodium polysulfide with bis(2-chloroethyl formal). 

Sodium polysulfide and bis(2-chloroethyl)formal are used to produce ST polysulfide rubber. Products made from these rubbers exhibit outstanding resistance to gas permeation, ozone, and weathering. When compounded with carbon black the ST rubbers are resistant to UV light and sunlight. The resistance of ST rubber to ozone can be improved by the addition of nickel dibutyldithiocarbamate (NBC) however, this addition can degrade the materials compression set. 

The FA polysulfide rubbers are prepared by reacting a mixture of bis(2-chloroethyl)formal and ethylene dichloride with sodium polysulfide. Cured compounds have exceptionally low permeability to gases, water, and organic liquids and exhibit excellent low-temperature flexibility. The FA polysulfide rubber compounds display excellent resistance to ozone, weathering, and exposure to UV light. In general, their resistance is superior to that of the ST polysulfide rubbers. If high concentrations of ozone are to be present, the use of 0.5 part of NBC per 100 parts FA polysulfide rubber will improve the ozone resistance. 

ST polysulfide rubber is a millable gum elastomer prepared from bis (2-chloroethyl) formal and sodium polysulfide. Vulcanizates exhibit outstanding resistance to a broad spectrum of oils and solvents, to gas permeability, low temperature, ozone and weathering. Typical uses include gas meter diaphragms, rollers, printing blankets, o-rings, and many specialty molded items. 

Since the mercaptide group is regenerated, the interchange can continue until a major part of the polymer is volatilized [16]. Pyrolysis of cured polysulfide polymers based on bis(2-chloroethyl)formal has so been studied under GC-MS conditions by Rama Rao et aL [81]. Apart fr( n the cyclic monomer, appreciable amounts of other compounds are also formed. The breaking of formal bond was found to be the initiation step. 

The general preparation of polysulfide liquid polymers, as discussed by Patrick and Ferguson involves first the reaction of bis-chloroethyl formal with a sodium polysulfide solution containing specific emulsifying and nucleating agents as shown below ... 

---