Process for producing polymers having terminal functional group

Details Process for producing polymers having terminal functional group Process for producing polymers having terminal functional group

1995-11-21

1998-12-08

Henderson, Christopher

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

526214, 526220, 526222, 526223, C08F 440, C08F 200

Patent

active

058470611

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a process for producing polymers having on one end or both ends thereof a mercapto, amino, hydroxyl, carboxyl, isocyanate or like functional groups which may be protected.


BACKGROUND ART

There have been proposed several processes for producing, by radical polymerization, polymers having a terminal functional group such as mercapto, amino, hydroxyl, carboxyl or isocyanate group.
Known processes for producing polymers having a terminal mercapto group include the following.
1 One which comprises photopolymerizing a radical-polymerizable monomer in the presence of a tetraalkylthiuram disulfide or dibenzoyl disulfide and then treating the obtained polymer having terminal thiocarbamate group or thiobenzoate group with an acid or alkali ("Makromolekular Chemie, Rapid Communications" 3, 127 (1982) or Journal of Japan Rubber Association 59, No. 12, 658 (1986), hereinafter this process is referred to as "Process A").
2 One which comprises, utilizing ready addition of mercapto group to double bond such as olefin, permitting a thio-S-carboxylic acid to add to a polymer having terminal double bond and treating the obtained polymer having terminal thio-S-carbonate group with an acid or alkali ("Makromoleckular Chemie, Symposia" 48/49, 317 (1991), hereinafter referred to as "Process B").
3 One which comprises polymerizing a radical-polymerizable monomer in the presence of a thio-S-carboxylic acid and with an initiator of azobisisobutyronitrile (hereinafter abbreviated as AIBN) and treating the obtained polymer having terminal thio-S-carbonate group with an acid or alkali (Japanese Patent Application Laid-open No. 187005/1984, hereinafter referred to as "Process C").
Known processes for producing polymers having a terminal amino,isocyanate,hydroxyl or carboxyl group include the following.
4 One which comprises polymerizing a radical-polymerizable monomer in the presence of the hydrochloric acid salt of mercaptoethylamine, to obtain a polymer having amino group on one end thereof ("Journal Polymer Science Part A Polymer Chemistry" 27, 2007 (1989), hereinafter referred to as "Process D").
5 One which comprises polymerizing t-butyl acrylate in the presence of 4,4'-diaminodiphenyl disulfide and with an initiator of AIBN and hydrolyzing the resulting polymer, to obtain a polyacrylic acid having amino group on both ends thereof ("Macromolecules" 26, 2240 (1993), hereinafter referred to as "Process E").
6 One which comprises photopolymerizing a radical-polymerizable monomer in the presence of 4,4'-diamino-diphenyl disulfide or 4,4'-diisocyanatediphenyldisulfide, to obtain a polymer having amino group or isocyanate group on both ends thereof ("Kobunshi-kagaku" 26, No. 286, 148 (1969), hereinafter referred to as "Process F").
7 One which comprises polymerizing a radical-polymerizable monomer with an initiator of hydrogen peroxide, to obtain a polymer having hydroxyl group on one end or both ends thereof (Japanese Patent Application Laid-open No. 75912/1984, hereinafter referred to as "Process G").
8 One which comprises polymerizing a radical-polymerizable monomer in the presence of 4,4'-azobis-4-cyanovaleric acid and dithioglycolic acid, to obtain a polymer having hydroxyl group on both ends thereof ("Polymer Preprints, Japan" 36, No. 6, 1637 (1987), hereinafter referred to as "Process H").
Process A is not applicable to all radical-polymerizable monomers and cannot be applied to acrylonitrile, vinyl acetate, vinylidene chloride or the like. Besides, this process, which uses light-irradiation polymerization, has the problems of difficulty in controlling polymerization rate and heat removal and has hence not been used on a commercial scale. Process B requires previous preparation of a polymer having terminal double bond, which increases the number of reaction steps and thus raises the production cost. Process C can introduce mercapto group into only one end of the polymer and further has the problem that increasing the polymerization rate results in a lowered ratio of introductio

REFERENCES:
patent: 2396997 (1946-03-01), Fryling
patent: 3337518 (1967-08-01), Serniuk
patent: 4013824 (1977-03-01), Uraneck et al.
patent: 4027090 (1977-05-01), Giddings
patent: 4988781 (1991-01-01), McKinney

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