Radical Initiation 2017/2/ ) Thermal Decomposition of Initiators
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1 adical Initiation Production of radicals (from initiator) to initiate chain polymerization. A variety of initiator systems can be used to bring about the radical polymerization. 1) Thermal Decomposition of Initiators 2) edox Initiation 3) Photochemical Initiation 4) Initiation by Ionizing adiation 5) Pure Thermal Initiation 6) ther Methods of Initiation 2017/2/21 1 1) Thermal Decomposition of Initiators (Thermal initiated or thermal catalyzed polymerization) Thermal, homolytic dissociation of initiators with bond dissociation energy = 100 ~ 170 kj/mol (-, S-S, N-). * Type of Initiators (a) Peroxides Acyl peroxides: acetyl peroxide (70~70 o C) benzoyl peroxide (80~95 o C) Alkyl peroxides cumyl peroxide (140~160 o C) di-t-butyl peroxide (120~140 o C) Hydroperoxides Peresters Acyl peroxide: Alkyl peroxide: ' Hydroperoxide: H Perester: C C C ' ' 2017/2/21 2
2 Commonly used at o C o C o C 2017/2/21 3 (b) Azo Compounds 2,2 -azobisisobutyronitrile (AIBN) (50~70 o C) (c) Disulphides & Tetrazenes: S-S 2S. k I d 2. 2 N-N=N-N N. + N 2 Used at temp. where k d = 10-4 ~10-6 sec -1. -d[i]/dt = k d [I] [I] = [I o ]e -k d t or log([i o ]/[I]) = k d t Initiator half-life: t 1/2 = 0.693/k d 2017/2/21 4
3 The various initiators are used at different temperatures depending on their rates of decomposition. Temperature used: (with k d = 10-4 ~10-6 sec -1 ) AIBN: ; Acetyl peroxide: ; Benzoyl peroxide: Dicumyl or di-t-butyl peroxide: /2/21 5 * Kinetics of Initiation and Polym. d = 2fk d [I] = i f: initiator efficiency p = k p [M]( i /2k t ) 1/2 = k p [M](fk d [I]/k t ) 1/2. (3-32) initiator efficiency (f): the fraction of the radicals produced in the thermal homolysis that initiate polymer chains. Initiation: I M M 1. Deviation from [I] 1/2 due to: 1) Decreased f with increasing [I]. 2) Primary termination. M n. +. K tp M n If termination occurs exclusively by primary termination: p = k p k i [M] 2 /k tp p is independent of [I]. 2017/2/21 6
4 Deviation from [M] due to (higher than first-order): 1) i depends on [M]: f = f [M] 2) Monomer-induced homolysis: M + I M /2/21 7 2) edox Initiation (r redox catalyst, redox activation) adical production occurs at a reasonable rates over a very wide range of temperatures (0~50 o C). Some redox polymerization can be initiated photolytically as well as thermally. * Types of edox Initiators (1) Peroxides + educing agents (Fe 2+, Cr 2+, V 2+, Ti 3+, Co 2+, Cu +, ) H Fe 2+ H - + H. + Fe 3+ + Fe H + Fe 2+ H - +. C + Fe 2+ C - +. (2) Inorganic (reductants + oxidants) 2- S Fe 2+ Fe 3+ + S S S S 2 3 S S S 2-3. (3) rganic-inorganic edox Pairs -CH 2 -H + Ce 4+ Ce 3+ + H + + -C. H-H (4) Monomer as edox component N,N-dimethylaniline + MMA 2017/2/21 8
5 H Fe 2+ H - + H. + Fe 3+ + Fe Fe 3+ H + Fe 2+ H Fe 3+ C' + Fe 2+ 'C Fe 3+ Must be in aqueous or emulsion. C C + N BP Can be in organic solvent. + Ṅ + C. + C - For styrene polymerization: k d = 1.25 x 10-2 l/mol.sec at 60 o C k d = 2.29 x 10-3 l/mol.sec at 30 o C But BP: k d = 1.33 x 10-4 l/mol.sec at 90 o C 2017/2/21 9 * ate of edox Polymerization Bimolecular termination: i = k d [reductant][oxidant] p = k p [M]( i /2k t ) 1/2 = k p [M](k d [reductant][oxidant]/2k t ) 1/2 Monomolecular termination: M n. + Ce 4+ Ce 3+ + H + + dead polymer i = k d [Ce 4+ ][alcohol] t = k t [Ce 4+ ][M. ] p = k d k p [M] [alcohol] /k t 2017/2/21 10
6 3) Photochemical Initiation Photochemical or photoinitiated polymerization: radicals are produced by UV and visible light irradiation. (excitation) Photosensitizer( 光增感劑 ): increase rate or red-shift wavelength. Advantages: * Spatially directed. * Turn on-off by light. * Initiation rate can be controlled by light intensity and radical source. * Solvent-free. Drawbacks: * Limited to surface-type application. Applications: * Printing and coating (acrylates). * Photolithography: photo-resist ( 光阻劑 ) in IC & PC. 2017/2/21 11 contrast of a photoresist: the development rate as a function of the absorbed light dose. Contrast ( 對比 ) for positive resist: = [log(d p /D p o )] -1 negative resist: = [log(d x /D x o )] -1 contrast curve 2017/2/21 12
7 Bulk monomer (absorption > nm and low quantum yield) Irradiation of thermal and edox Initiators A useful photoinitiator should absorb strongly in the wavelength range of the light source and possess a high quantum yield for radical production. Aromatic ketones: benzophenone & acetophenone, and their derivatives. -Scission: 2) e-transfer: 3) Direct H-transfer from H to ketone. 2 N-CH 2 : tertiary amines with -hydrogen are the most effective. ther e-donors: alcohols, amides, amino acids, and ethers. 2017/2/21 13 Benzoin benzyl ketal aroylphosphine oxide -aminoalkylphenone ate of photoinitiation: i = 2 I a I a : intensity of absorbed light (moles of light quanta/l-sec) quantum yield of initiation: no of propagating chains initiated per light photon absorbed. p = k p [M]( i /2k t ) = k p [M] ( I a /k t ) 1/2 2017/2/21 14
8 4) Initiation by Ionizing adiations (10 kev~100 mev) Electrons ( -rays), neutrons, -particles (He 2+ ). Both radical and ionic polymerizations are possible depending on water content. For styrene monomer: [H 2 ] ~ M: radical polymerization only. < M: bimodal MWD (both radical and cationic) < M: unimodal MWD (cationic) High penetration power but dangerous. C + radiation C +. + e - e - B. A. + B + e- 5) Pure Thermal Initiation C - B. + A - 2 CH=CH 2 styrene. CHCH 3 +. A. + e - H H H Diels-Alder dimer Add inhibitor (hydroquinone, etc.) during storage to prevent thermal polymerization. 2017/2/21 15 Initiator Efficiency (f < 1) The fraction of radicals, formed in the primary step of initiator decomposition, which are successful in initiating polymerization. Wastage of initiator: (1)Induced decomposition of initiator (chain transfer to initiator). M n. + -C-C- M n -C- + -C. (2)Side reaction of the radicals formed in the primary step of initiator decomposition. (f) The initiator efficiency is considered exclusive of any initiator wastage by induced decomposition. When neglects the occurrence of induced decomposition: effective or practical initiator efficiency = net or overall initiation efficiency of the initial catalyst concentration. 2017/2/21 16
9 Mechanism: Cage Effect (f = 0.3~0.8) C-C [2 C. ] [ ]: solvent cage [2 C. ] [ C + C 2 ] [2 C. ] + M C. + CM. initiation [2 C. ] 2 C. C. + M CM. initiation C.. + C 2. + M M. initiation. + C. C 2. - [. ] ~ 10 M, k = 10 7 l/mol-sec, life-time = sec. f is constant at high monomer conc., but it decreases with decreasing monomer conc. and increasing initiation rate. (Fig. 3-5) Exception (non-paired radicals): Fe 2+ + H 2 2 Fe 3+ + H - + H. 2017/2/21 17 ut the solvent cage, the preference for initiation of polymerization arises from the much greater [M] (10-1 ~10 M) than [M n. ] (10-7 ~10-9 M). f decreases during the course of a polymerization: due to decreasing [M] and increasing viscosity. Experimental Determination of Initiator Efficiency (f): 1) Determination and comparison of both the initiator decomposition and production of polymer molecules (X n ). 2) Direct analysis of polymer end groups. 3) Use of radical scavengers, such as * stable radicals: DPPH, TEMP, 1,3,5-triphenylverdazyl,...etc. 2017/2/21 18
10 N 2 H N Ṅ N 2 +. N N N 2 N 2 N 2 N 2 DPPH radical Deep violet Light yellow or colorless * Fast hydrogen or halogen transfer: thiols, bromine, dihydroanthracene. * Molecules react with radicals (spin traps): ES spectroscopy. p-benzoquinone, duroquinone, nitroso & nitrone compounds (spin traps). 4) Dead-end polymerization (determine f and k d ) Very low [I] so that half-life of the propagating polymer chains approximates that of the initiator. - ln{1- [ln(1-p)/ln(1-p )]} = k d t/2 (Fig. 3-6) 2017/2/21 19 p = -d[m]/dt = k p [M](fk d [I]/k t ) 1/2 -d[m]/[m] = k p (fk d [I]/k t ) 1/2 dt [I] = [I o ]e -k d t -ln([m]/[m] o ) = -ln(1-p) = 2k p (f[i] o /k t k d ) 1/2 (1- e -k d t ) (3-92) At long reaction time (t ): Where p = ([M] o -[M])/[M] o : extent of conversion. -ln([m] /[M] o ) = -ln(1-p ) = 2k p (f[i] o /k t k d ) 1/ (3-93) Divide (3-92) by (3-93), rearrange, and then take logarithms of both sides: - ln{1- [ln(1-p)/ln(1-p )]} = k d t/2 The k d can be obtained from the slope (k d /2), then f can be obtained from equation 3-32 or 3-93 if the ratio k p /k t 1/2 is known. p = k p [M]( i /2k t ) 1/2 = k p [M](fk d [I]/k t ) 1/ (3-32) 2017/2/21 20
11 2017/2/21 21
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