Skip to main content

Synthesis of Terpene-Based Polymers

  • Chapter
  • First Online:

Part of the book series: Advances in Polymer Science ((POLYMER,volume 253))

Abstract

Terpenes or terpenoids are a large class of diverse biological compounds derived from isoprene. Due to their abundance in nature and desirable properties, there has been great interest in producing polymers with terpenes as either functional entities or as the main constituent. Terpene-based polymers have found applications as biomedical or liquid crystalline materials and, more importantly, have greatly contributed to the concept of sustainable polymer chemistry. The design and preparation of terpene-based polymers have involved different chemical strategies and a wide variety of polymerization techniques, making use of the chemical functionalities in terpene molecules, e.g. (conjugated) double bonds, hydroxyl and carboxyl groups. This review describes the synthetic methodologies for terpene-based polymers, classified by the position of terpene entities in the polymer chains, i.e., main chain, terminal or central group, and pendant group.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Abbreviations

Ac:

Acetyl

ADMET:

Acyclic diene metathesis

AIBN:

α,α′-Azobisisobutyronitrile

ATRP:

Atom transfer radical polymerization

BPO:

Benzoyl peroxide

Bui :

Isobutyl

Bz:

Benzyl

CDI:

1,1-Carbonyldiimidazole

Chol:

Cholesterol or cholesteryl

CholCl:

Cholesteryl chloroformate

Cy:

Cyclohexyl

DCC:

Dicyclohexylcarbodiimide

DMAP:

4-(N,N-Dimethylamino)pyridine

DMF:

N,N-Dimethylformamide

DMSO:

Dimethylsulfoxide

Et:

Ethyl

LC:

Liquid crystal/crystalline

mCPBA:

m-Chloroperbenzoic acid

Me:

Methyl

Men:

Menthol

MMA:

Methyl methacrylate

M n :

Number-average molecular weight

MW:

Molecular weight

NHS:

N-Hydroxysuccinimide

Oct:

Octoate

PCL:

Poly(ε-caprolactone)

PDI:

Polydispersity index

PEG:

Poly(ethylene glycol)

PEO:

Poly(ethylene oxide)

Ph:

Phenyl

PLA:

Poly(lactic acid)

PNIPAM:

Poly(N-isopropylacrylamide)

Pr:

Propyl

pTSA:

p-Toluenesulfonic acid

Py:

Pyridine

RAFT:

Reversible addition-fragmentation chain transfer

ROMP:

Ring-opening metathesis polymerization

ROP:

Ring-opening polymerization

TBD:

1,5,7-Triazabicyclo[4.4.0]dec-5-ene

T g :

Glass transition temperature

THF:

Tetrahydrofuran

References

  1. Klok HA (2005) J Polym Sci A Polym Chem 43:1

    CAS  Google Scholar 

  2. Lutz J-F, Börner HG (2008) Prog Polym Sci 33:1

    CAS  Google Scholar 

  3. van Hest J, Sumerlin B (2011) Polym Chem 2:1427

    Google Scholar 

  4. Fuks G, Talom RM, Gauffre F (2011) Chem Soc Rev 40:2475

    CAS  Google Scholar 

  5. Bhattarai N, Gunn J, Zhang M (2010) Adv Drug Deliv Rev 62:83

    CAS  Google Scholar 

  6. Bertin A, Hermes F, Schlaad H (2010) Adv Polym Sci 224:167

    CAS  Google Scholar 

  7. van Dongen SFM, de Hoog HPM, Peters R, Nallani M, Nolte RJM, van Hest JCM (2009) Chem Rev 109:6212

    Google Scholar 

  8. Pasut G, Veronese FM (2009) Adv Drug Deliv Rev 61:1177

    CAS  Google Scholar 

  9. Alemdaroglu FE, Herrmann A (2007) Org Biomol Chem 5:1311

    CAS  Google Scholar 

  10. Schlaad H, Antonietti M (2003) Eur Phys J E 10:17

    CAS  Google Scholar 

  11. Greenwald RB, Choe YH, McGuire J, Conover CD (2003) Adv Drug Deliv Rev 55:217

    CAS  Google Scholar 

  12. Breitmaier E (2006) Terpenes: flavors, fragrances, pharmaca, pheromones. Wiley-VCH, Weinheim

    Google Scholar 

  13. Sun IC, Wang H-K, Kashiwada Y, Shen J-K, Cosentino LM, Chen C-H, Yang L-M, Lee K-H (1998) J Med Chem 41:4648

    CAS  Google Scholar 

  14. Cichewicz RH, Kouzi SA (2004) Med Res Rev 24:90

    CAS  Google Scholar 

  15. Hayek EWH, Jordis U, Moche W, Sauter F (1989) Phytochemistry 28:2229

    CAS  Google Scholar 

  16. Zhu XX, Nichifor M (2002) Acc Chem Res 35:539

    CAS  Google Scholar 

  17. Gautrot JE, Zhu XX (2009) J Mater Chem 19:5705

    CAS  Google Scholar 

  18. Chandrawati R, Stadler B, Postma A, Connal LA, Chong SF, Zelikin AN, Caruso F (2009) Biomaterials 30:5988

    CAS  Google Scholar 

  19. Xu H, Wang KQ, Deng YH, da Chen W (2010) Biomaterials 31:4757

    CAS  Google Scholar 

  20. Oba M, Miyata K, Osada K, Christie RJ, Sanjoh M, Li W, Fukushima S, Ishii T, Kano MR, Nishiyama N, Koyama H, Kataoka K (2011) Biomaterials 32:652

    CAS  Google Scholar 

  21. Guo JB, Sun J, Li KX, Cao H, Yang H (2008) Liq Cryst 35:87

    CAS  Google Scholar 

  22. Guo JB, Sun J, Zhang LP, Li KX, Cao H, Yang H, Zhu SQ (2008) Polym Adv Technol 19:1504

    CAS  Google Scholar 

  23. Yang PC, Liu JH (2008) J Disp Technol 4:369

    CAS  Google Scholar 

  24. Meng FB, Lian J, Chen HB, Gao YM, Zhang BY (2009) High Perform Polym 21:64

    CAS  Google Scholar 

  25. Ahn S-k, Deshmukh P, Gopinadhan M, Osuji CO, Kasi RM (2011) ACS Nano 5:3085

    CAS  Google Scholar 

  26. Gandini A (2008) Macromolecules 41:9491

    CAS  Google Scholar 

  27. Hadjichristidis N, Pitsikalis M, Pispas S, Iatrou H (2001) Chem Rev 101:3747

    CAS  Google Scholar 

  28. Osakada K, Takeuchi D (2004) Adv Polym Sci 171:137

    CAS  Google Scholar 

  29. Swiezewska E, Danikiewicz W (2005) Prog Lipid Res 44:235

    CAS  Google Scholar 

  30. Puskas JE, Gautriaud E, Deffieux A, Kennedy JP (2006) Prog Polym Sci 31:533

    CAS  Google Scholar 

  31. Nishiura M, Hou Z (2010) Nat Chem 2:257

    CAS  Google Scholar 

  32. Runckel WJ, Goldblatt LA (1946) Ind Eng Chem 38:749

    CAS  Google Scholar 

  33. Cawse JL, Stanford JL, Still RH (1987) J Appl Polym Sci 33:2217

    Google Scholar 

  34. Marvel CS, Hwa CCL (1960) J Polym Sci 45:25

    CAS  Google Scholar 

  35. Trumbo DL (1993) Polym Bull 31:629

    CAS  Google Scholar 

  36. Johanson AJ, McKennon FL, Goldblatt LA (1948) Ind Eng Chem 40:500

    CAS  Google Scholar 

  37. Gleason AH, Nelson JF (1958) Synthetic drying oils by copolymerization of diolefins with myrcene. US Patent 2829065

    Google Scholar 

  38. Sivola A (1977) The n-butyllithium-initiated polymerization of myrcene and its copolymerization with styrene. Acta Polytechnica Scand, Chem Incl Metall Ser No 134

    Google Scholar 

  39. Quirk RP (1983) Triblock polymers of a monovinyl aromatic compound and myrcene. US Patent 4374957

    Google Scholar 

  40. Rummelsburg AL (1945) Polymerized acyclic terpenes and method of production. US Patent 2373419

    Google Scholar 

  41. Veazey RL (1987) Polyalloocimene and methode for the preparation thereof. US Patent 4694059

    Google Scholar 

  42. Rummelsburg AL (1945) Terpene resins. US Patent 2383084

    Google Scholar 

  43. Marvel CS, Kiener PE, Vessel ED (1959) J Am Chem Soc 81:4694

    CAS  Google Scholar 

  44. Marvel CS, Kiener PE (1962) J Polym Sci 61:311

    CAS  Google Scholar 

  45. Jones JF (1958) J Polym Sci 33:513

    CAS  Google Scholar 

  46. Priola A, Corno C, Bruzzone M, Cesca S (1981) Polym Bull 4:743

    CAS  Google Scholar 

  47. Srivastava AK, Pandey P (2001) Polym Int 50:937

    CAS  Google Scholar 

  48. Pandey P, Srivastava AK (2002) J Polym Sci A Polym Chem 40:1243

    CAS  Google Scholar 

  49. Pathak S, Srivastava AK (2009) J Appl Polym Sci 112:2601

    CAS  Google Scholar 

  50. Pandey P, Srivastava K (2003) Des Monomers Polym 6:197

    CAS  Google Scholar 

  51. Srivastava AK, Pandey P, Mishra G (2006) J Appl Polym Sci 102:4908

    CAS  Google Scholar 

  52. Pandey P, Srivastava AK (2002) Adv Polym Tech 21:59

    CAS  Google Scholar 

  53. Srivastava AK, Pandey P (2002) Eur Polym J 38:1709

    CAS  Google Scholar 

  54. Sharma S, Srivastava AK (2008) J Appl Polym Sci 108:892

    CAS  Google Scholar 

  55. Misra G, Srivastava A (2008) Colloid Polym Sci 286:445

    CAS  Google Scholar 

  56. Shukla A, Srivastava AK (2004) Polym Adv Technol 15:445

    CAS  Google Scholar 

  57. Shukla A, Srivastava AK (2004) J Appl Polym Sci 92:1134

    CAS  Google Scholar 

  58. Shukla A, Srivastava A (2003) J Macromol Sci Part A Pure Appl Chem 40:61

    Google Scholar 

  59. Shukla A, Srivastava AK (2003) High Perform Polym 15:243

    CAS  Google Scholar 

  60. Shukla A, Srivastava AK (2002) Polym Plast Technol Eng 41:777

    CAS  Google Scholar 

  61. Yadav S, Srivastava AK (2004) Polym Plast Technol Eng 43:1229

    CAS  Google Scholar 

  62. Yadav S, Srivastava AK (2002) J Polym Res 9:265

    CAS  Google Scholar 

  63. Yadav S, Srivastava AK (2007) J Appl Polym Sci 103:476

    CAS  Google Scholar 

  64. Yadav S, Srivastava AK (2006) Indian J Chem Technol 13:283

    CAS  Google Scholar 

  65. Mishra G, Srivastava AK (2007) Polym Bull 58:351

    CAS  Google Scholar 

  66. Roberts WJ, Day AR (1950) J Am Chem Soc 72:1226

    CAS  Google Scholar 

  67. Modena M, Bates RB, Marvel CS (1965) J Polym Sci Part A Gen Pap 3:949

    CAS  Google Scholar 

  68. Doiuchi T, Yamaguchi H, Minoura Y (1981) Eur Polym J 17:961

    CAS  Google Scholar 

  69. Sharma S, Srivastava A (2003) Polym Plast Technol Eng 42:485

    CAS  Google Scholar 

  70. Sharma S, Srivastava A (2003) J Macromol Sci Part A Pure Appl Chem 40:593

    Google Scholar 

  71. Sharma S, Srivastava AK (2004) Eur Polym J 40:2235

    CAS  Google Scholar 

  72. Sharma S, Srivastava AK (2006) Des Monomers Polym 9:503

    CAS  Google Scholar 

  73. Sharma S, Srivastava AK (2007) J Appl Polym Sci 106:2689

    CAS  Google Scholar 

  74. Sharma S, Srivastava AK (2004) J Appl Polym Sci 91:2343

    CAS  Google Scholar 

  75. Mishra G, Srivastava AK (2006) J Appl Polym Sci 102:4595

    CAS  Google Scholar 

  76. Byrne CM, Allen SD, Lobkovsky EB, Coates GW (2004) J Am Chem Soc 126:11404

    CAS  Google Scholar 

  77. Mathers RT, Damodaran K, Rendos MG, Lavrich MS (2009) Macromolecules 42:1512

    CAS  Google Scholar 

  78. Mathers RT, McMahon KC, Damodaran K, Retarides CJ, Kelley DJ (2006) Macromolecules 39:8982

    CAS  Google Scholar 

  79. Satoh K, Sugiyama H, Kamigaito M (2006) Green Chem 8:878

    CAS  Google Scholar 

  80. Carmody MO, Carmody WH (1937) J Am Chem Soc 59:1312

    CAS  Google Scholar 

  81. Vohwinkel F (1967) Alpha-pinene polymerization. US Patent 3313865

    Google Scholar 

  82. Khan AR, Yousufzai AHK, Jeelani HA, Akhter T (1985) J Macromol Sci Chem A22:1673

    CAS  Google Scholar 

  83. Deng YX, Peng CP, Liu P, Lu J, Zeng LM, Wang LC (1996) J Macromol Sci Pure Appl Chem A 33:995

    Google Scholar 

  84. Kennedy J, Chou T (1976) Adv Polym Sci 21:1

    CAS  Google Scholar 

  85. Snyder C, McIver W, Sheffer H (1977) J Appl Polym Sci 21:131

    CAS  Google Scholar 

  86. Kennedy JP, Liao TP, Guhaniyogi S, Chang VSC (1982) J Polym Sci A Polym Chem 20:3219

    CAS  Google Scholar 

  87. Keszler B, Kennedy J (1992) Adv Polym Sci 100:1

    CAS  Google Scholar 

  88. Kukhta NA, Vasilenko IV, Kostjuk SV (2011) Green Chem 13:2362

    CAS  Google Scholar 

  89. Malpass JGD (1984) Polymerization of beta-pinene. US Patent 4487901

    Google Scholar 

  90. Kennedy JP, Liao TP, Guhaniyogi S, Chang VSC (1982) J Polym Sci A Polym Chem 20:3229

    CAS  Google Scholar 

  91. Sheffer H, Greco G, Paik G (1983) J Appl Polym Sci 28:1701

    CAS  Google Scholar 

  92. Pietila H, Sivola A, Sheffer H (1970) J Polym Sci Part A-1 Polym Chem 8:727

    CAS  Google Scholar 

  93. Maslinskasolich J, Rudnicka I (1988) Eur Polym J 24:453

    CAS  Google Scholar 

  94. Bates TH, Best JVF, Williams TF (1962) J Chem Soc 1962:1531

    Google Scholar 

  95. Bates TH, Williams TF, Best JVF (1962) J Chem Soc 1962:1521

    Google Scholar 

  96. Zhang DH, Hillmyer MA, Tolman WB (2005) Biomacromolecules 6:2091

    CAS  Google Scholar 

  97. Wanamaker CL, O'Leary LE, Lynd NA, Hillmyer MA, Tolman WB (2007) Biomacromolecules 8:3634

    CAS  Google Scholar 

  98. Wanamaker CL, Bluemle MJ, Pitet LM, O'Leary LE, Tolman WB, Hillmyer MA (2009) Biomacromolecules 10:2904

    CAS  Google Scholar 

  99. Shin J, Martello MT, Shrestha M, Wissinger JE, Tolman WB, Hillmyer MA (2011) Macromolecules 44:87

    CAS  Google Scholar 

  100. Ruzicka L (1920) Helv Chim Acta 3:781

    CAS  Google Scholar 

  101. Treibs W (1933) J Prakt Chem 138:299

    CAS  Google Scholar 

  102. Lowe JR, Martello MT, Tolman WB, Hillmyer MA (2011) Polym Chem 2:702

    CAS  Google Scholar 

  103. Lowe JR, Tolman WB, Hillmyer MA (2009) Biomacromolecules 10:2003

    CAS  Google Scholar 

  104. Gautrot JE, Zhu XX (2006) Angew Chem Int Ed 45:6872

    CAS  Google Scholar 

  105. Gautrot JE, Zhu XX (2009) Macromolecules 42:7324

    CAS  Google Scholar 

  106. Gautrot JE, Zhu XX (2008) Chem Commun 1674

    Google Scholar 

  107. Ahlheim M, Hallensleben ML (1988) Makromol Chem Rapid Commun 9:299

    CAS  Google Scholar 

  108. Noll O, Ritter H (1996) Macromol Rapid Commun 17:553

    CAS  Google Scholar 

  109. Zuluaga F, Valderruten NE, Wagener KB (1999) Polym Bull 42:41

    CAS  Google Scholar 

  110. Gouin S, Zhu XX, Lehnert S (2000) Macromolecules 33:5379

    CAS  Google Scholar 

  111. Abate DW, Stevens MP (1992) J Appl Polym Sci 46:389

    CAS  Google Scholar 

  112. Jeromenok J, Böhlmann W, Antonietti M, Weber J (2011) Macromol Rapid Commun 32:1846

    CAS  Google Scholar 

  113. Firdaus M, de Montero Espinosa L, Meier MAR (2011) Macromolecules 44:7253

    CAS  Google Scholar 

  114. van de Manakker F, van der Pot M, Vermonden T, van Nostrum CF, Hennink WE (2008) Macromolecules 41:1766

    Google Scholar 

  115. van de Manakker F, Vermonden T, el Morabit N, van Nostrum CF, Hennink WE (2008) Langmuir 24:12559

    Google Scholar 

  116. van de Manakker F, Kroon-Batenburg LMJ, Vermonden T, van Nostrum CF, Hennink WE (2010) Soft Matter 6:187

    Google Scholar 

  117. Yang DB, Zhu JB, Huang ZJ, Ren HX, Zheng ZJ (2008) Colloids Surf B 63:192

    CAS  Google Scholar 

  118. Beugin S, Edwards K, Karlsson G, Ollivon M, Lesieur S (1998) Biophys J 74:3198

    CAS  Google Scholar 

  119. Liu L, Guo K, Lu J, Venkatraman SS, Luo D, Ng KC, Ling EA, Moochhala S, Yang YY (2008) Biomaterials 29:1509

    CAS  Google Scholar 

  120. Liu X-M, Yang Y-Y, Leong KW (2003) J Colloid Interface Sci 266:295

    CAS  Google Scholar 

  121. Chaw CS, Chooi KW, Liu XM, Tan CW, Wang L, Yang YY (2004) Biomaterials 25:4297

    CAS  Google Scholar 

  122. Kostakis K, Mourmouris S, Charalabidis D, Pitsikalis M (2003) Eur Phys J E 10:55

    CAS  Google Scholar 

  123. Javakhishvili I, Binder WH, Tanner S, Hvilsted S (2010) Polym Chem 1:506

    CAS  Google Scholar 

  124. Schlaad H, Diehl C, Gress A, Meyer M, Demirel AL, Nur Y, Bertin A (2010) Macromol Rapid Commun 31:511

    CAS  Google Scholar 

  125. Ray JG, Ly JT, Savin DA (2011) Polym Chem 2:1536

    CAS  Google Scholar 

  126. Huh KM, Lee KY, Kwon IC, Kim Y-H, Kim C, Jeong SY (2000) Langmuir 16:10566

    CAS  Google Scholar 

  127. Zou T, Li S-L, Zhang X-Z, Wu X-J, Cheng S-X, Zhuo R-X (2007) J Polym Sci A Polym Chem 45:5256

    CAS  Google Scholar 

  128. Kim C, Lee SC, Kang SW, Kwon IC, Kim YH, Jeong SY (2000) Langmuir 16:4792

    CAS  Google Scholar 

  129. Chen W-Q, Wei H, Li S-L, Feng J, Nie J, Zhang X-Z, Zhuo R-X (2008) Polymer 49:3965

    CAS  Google Scholar 

  130. Bekkara-Aounallah F, Gref R, Othman M, Reddy LH, Pili B, Allain V, Bourgaux C, Hillaireau H, Lepêtre-Mouelhi S, Desmaële D, Nicolas J, Chafi N, Couvreur P (2008) Adv Funct Mater 18:3715

    CAS  Google Scholar 

  131. Greenwald RB, Gilbert CW, Pendri A, Conover CD, Xia J, Martinez A (1996) J Med Chem 39:424

    CAS  Google Scholar 

  132. Greenwald RB, Pendri A, Bolikal D, Gilbert CW (1994) Biorg Med Chem Lett 4:2465

    CAS  Google Scholar 

  133. Hofmann AM, Wurm F, Hühn E, Nawroth T, Langguth P, Frey H (2010) Biomacromolecules 11:568

    CAS  Google Scholar 

  134. Hofmann AM, Wurm F, Frey H (2011) Macromolecules 44:4648

    CAS  Google Scholar 

  135. Zhao J, Schlaad H, Weidner S, Antonietti M (2012) Polym Chem. doi: 10.1039/C1PY00388G

  136. Shiraishi K, Sugiyama M, Okamura Y, Sugiyama K (2007) J Appl Polym Sci 103:3064

    CAS  Google Scholar 

  137. Sugiyama K, Hanamura R, Sugiyama M (2000) J Polym Sci A Polym Chem 38:3369

    CAS  Google Scholar 

  138. Kricheldorf HR, Boettcher C (1993) Makromol Chem 194:1653

    CAS  Google Scholar 

  139. Kricheldorf HR, Kreiser-Saunders I (1994) Polymer 35:4175

    CAS  Google Scholar 

  140. Klok HA, Hwang JJ, Hartgerink JD, Stupp SI (2002) Macromolecules 35:6101

    CAS  Google Scholar 

  141. Klok HA, Hwang JJ, Iyer SN, Stupp SI (2002) Macromolecules 35:746

    CAS  Google Scholar 

  142. Zhang L, Wang QR, Jiang XS, Cheng SX, Zhuo RX (2005) J Biomater Sci Polym Ed 16:1095

    CAS  Google Scholar 

  143. Zou T, Cheng SX, Zhuo RX (2005) Colloid Polym Sci 283:1091

    CAS  Google Scholar 

  144. Zou T, Li F, Cheng SX, Zhuo RX (2006) J Biomater Sci Polym Ed 17:1093

    CAS  Google Scholar 

  145. Guo JB, Sun J, Cao H, Zhao DY, Yang H (2007) J Appl Polym Sci 105:3505

    CAS  Google Scholar 

  146. Guo J, Sun J, Cao H, Yang H (2008) J Incl Phenom Macrocycl Chem 60:95

    CAS  Google Scholar 

  147. Wan T, Liu Y, Yu J-Q, Chen S, Li F, Zhang X-Z, Cheng S-X, Zhuo R-X (2006) J Polym Sci A Polym Chem 44:6688

    CAS  Google Scholar 

  148. Luo J, Giguère G, Zhu XX (2009) Biomacromolecules 10:900

    CAS  Google Scholar 

  149. Strandman S, Le Dévédec F, Zhu XX (2011) Macromol Rapid Commun 32:1185

    CAS  Google Scholar 

  150. Giguère G, Zhu XX (2010) Biomacromolecules 11:201

    Google Scholar 

  151. Giguère G, Zhu XX (2007) J Polym Sci A Polym Chem 45:4173

    Google Scholar 

  152. Koyama Y, Ito T, Kimura T, Murakami A, Yamaoka T (2001) J Control Release 77:357

    CAS  Google Scholar 

  153. Liu X-M, Pramoda KP, Yang Y-Y, Chow SY, He C (2004) Biomaterials 25:2619

    CAS  Google Scholar 

  154. Liu X-M, Wang LS, Wang L, Huang JC, He CB (2004) Biomaterials 25:5659

    CAS  Google Scholar 

  155. Sung J, Park JM, Choi UH, Huh J, Jung B, Min BG, Ahn CH, Park C (2007) Macromol Rapid Commun 28:176

    CAS  Google Scholar 

  156. Thompson CJ, Ding CX, Qu XZ, Yang ZZ, Uchegbu IF, Tetley L, Cheng WP (2008) Colloid Polym Sci 286:1511

    CAS  Google Scholar 

  157. Lee EH, Kamigaito Y, Tsujimoto T, Uyama H, Sung MH (2010) J Microbiol Biotechnol 20:1424

    CAS  Google Scholar 

  158. Levit M, Nazarova O, Nekrasova T, Dobrodumov A, Anan’eva T, Nikiticheva A, Vlasova E, Pautov V, Panarin E (2010) Polym Sci Ser B 52:648

    Google Scholar 

  159. Wang Y, Wang LS, Goh SH, Yang YY (2007) Biomacromolecules 8:1028

    CAS  Google Scholar 

  160. Wang Y, Ke CY, Beh CW, Liu SQ, Goh SH, Yang YY (2007) Biomaterials 28:5358

    CAS  Google Scholar 

  161. Lee ALZ, Wang Y, Ye WH, Yoon HS, Chan SY, Yang YY (2008) Biomaterials 29:1224

    CAS  Google Scholar 

  162. Zang BL, Hu JS, Meng FB, Zhang BY (2004) J Appl Polym Sci 93:2511

    CAS  Google Scholar 

  163. Wang Y, Zhang BY, He XZ, Wang JW (2007) Colloid Polym Sci 285:1077

    CAS  Google Scholar 

  164. Hu JS, Yang LQ, Zhang X, Song ZW (2010) Liq Cryst 37:1259

    CAS  Google Scholar 

  165. Zhang BY, Hu JS, Jia YG, Du BG (2003) Macromol Chem Phys 204:2123

    CAS  Google Scholar 

  166. Zhang BY, Hu JS, Wang Y, Qian JH (2003) Polym J 35:476

    Google Scholar 

  167. Hu JS, Zhang BY, Yan G, He XZ (2004) J Polym Sci A Polym Chem 42:5262

    CAS  Google Scholar 

  168. Ganicz T, Pakula T, Fortuniak W, Bialecka-Florjanczyk E (2005) Polymer 46:11380

    CAS  Google Scholar 

  169. Mishra G, Srivastava AK (2007) J Macromol Sci Part A Pure Appl Chem 44:747

    CAS  Google Scholar 

  170. Tsuchida E, Yamamoto K, Miyatake K, Endo K (1997) Macromolecules 30:4235

    CAS  Google Scholar 

  171. Akiyoshi K, Ueminami A, Kurumada S, Nomura Y (2000) Macromolecules 33:6752

    CAS  Google Scholar 

  172. Akiyoshi K, Deguchi S, Moriguchi N, Yamaguchi S, Sunamoto J (1993) Macromolecules 26:3062

    CAS  Google Scholar 

  173. Kuroda K, Fujimoto K, Sunamoto J, Akiyoshi K (2002) Langmuir 18:3780

    CAS  Google Scholar 

  174. Morimoto N, Endo T, Iwasaki Y, Akiyoshi K (2005) Biomacromolecules 6:1829

    CAS  Google Scholar 

  175. Morimoto N, Endo T, Ohtomi M, Iwasaki Y, Akiyoshi K (2005) Macromol Biosci 5:710

    CAS  Google Scholar 

  176. Akiyama E, Morimoto N, Kujawa P, Ozawa Y, Winnik FM, Akiyoshit K (2007) Biomacromolecules 8:2366

    CAS  Google Scholar 

  177. Cui ZH, Zhang Y, He SJ (2008) Colloid Polym Sci 286:1553

    CAS  Google Scholar 

  178. de Visser AC, Feyen J, de Groot K, Bantjes A (1970) J Polym Sci Part B Polym Lett 8:805

    Google Scholar 

  179. Toth WJ, Tobolsky AV (1970) J Polym Sci Part B Polym Lett 8:289

    CAS  Google Scholar 

  180. De Visser AC, De Groot K, Feyen J, Bantjes A (1971) J Polym Sci Polym Chem Part A-1 Polym Chem 9:1893

    Google Scholar 

  181. De Visser AC, De Groot K, Feyen J, Bantjes A (1972) J Polym Sci Polym Lett Ed 10:851

    Google Scholar 

  182. Shannon PJ (1983) Macromolecules 16:1677

    CAS  Google Scholar 

  183. Hoyle CE, Chawla CP (1995) Macromolecules 28:1946

    CAS  Google Scholar 

  184. Yusa S, Kamachi M, Morishima Y (1998) Langmuir 14:6059

    CAS  Google Scholar 

  185. Hattori H, Uryu T (2000) J Polym Sci A Polym Chem 38:887

    CAS  Google Scholar 

  186. Lee YK, Onimura K, Tsutsumi H, Oishi T (2000) J Polym Sci A Polym Chem 38:4315

    CAS  Google Scholar 

  187. Mihara T, Uedaira T, Koide N (2002) Liq Cryst 29:855

    CAS  Google Scholar 

  188. Zhang BY, Hu JS, Zang BL, Zhou AJ (2003) J Appl Polym Sci 88:1936

    CAS  Google Scholar 

  189. Wang SF, Xu JW, Tong YJ, Wang L, He CB (2005) Polym Int 54:1268

    CAS  Google Scholar 

  190. Liu JH, Hung HJ, Yang PC, Tien KH (2008) J Polym Sci A Polym Chem 46:6214

    CAS  Google Scholar 

  191. Liu JH, Chiu YH, Chiu TH (2009) Macromolecules 42:3715

    CAS  Google Scholar 

  192. Liu J-H, Hsieh F-M (2009) Mater Chem Phys 118:506

    CAS  Google Scholar 

  193. Liu JH, Chou YL, Balamurugan R, Tien KH, Chuang WT, Wu MZ (2011) J Polym Sci A Polym Chem 49:770

    CAS  Google Scholar 

  194. Whitcombe MJ, Rodriguez ME, Villar P, Vulfson EN (1995) J Am Chem Soc 117:7105

    CAS  Google Scholar 

  195. Hamley IW, Castelletto V, Parras P, Lu ZB, Imrie CT, Itoh T (2005) Soft Matter 1:355

    CAS  Google Scholar 

  196. Jia L, Cao A, Levy D, Xu B, Albouy PA, Xing XJ, Bowick MJ, Li MH (2009) Soft Matter 5:3446

    CAS  Google Scholar 

  197. Jia L, Albouy P-A, Di Cicco A, Cao A, Li M-H (2011) Polymer 52:2565

    CAS  Google Scholar 

  198. Boisse S, Rieger J, Di-Cicco A, Albouy PA, Bui C, Li MH, Charleux B (2009) Macromolecules 42:8688

    CAS  Google Scholar 

  199. He SJ, Zhang Y, Cui ZH, Tao YZ, Zhang BL (2009) Eur Polym J 45:2395

    CAS  Google Scholar 

  200. Oishi T, Morikawa H, Matsusaki K, Fujimoto M (1994) Polym J 26:1332

    CAS  Google Scholar 

  201. Williamson SE, Kang D, Hoyle CE (1996) Macromolecules 29:8656

    CAS  Google Scholar 

  202. Seno KI, Date A, Kanaoka S, Aoshima S (2008) J Polym Sci A Polym Chem 46:4392

    CAS  Google Scholar 

  203. Moigne JL, Hilberer A, Kajzar F (1992) Makromol Chem 193:515

    Google Scholar 

  204. Yue D, Fujii T, Terada K, Tabei J, Shiotsuki M, Sanda F, Masuda T (2006) Macromol Rapid Commun 27:1460

    CAS  Google Scholar 

  205. Qu JQ, Shiotsuki M, Sanda F, Masuda T (2007) Macromol Chem Phys 208:823

    CAS  Google Scholar 

  206. Qu JQ, Suzuki Y, Shiotsuki M, Sanda F, Masuda T (2007) Macromol Chem Phys 208:1992

    CAS  Google Scholar 

  207. Iwasaki Y, Akiyoshi K (2006) Biomacromolecules 7:1433

    CAS  Google Scholar 

  208. Ahn S-k, Le Nguyen LT, Kasi RM (2009) J Polym Sci A Polym Chem 47:2690

    CAS  Google Scholar 

  209. Ahn S-k, Deshmukh P, Kasi RM (2010) Macromolecules 43:7330

    CAS  Google Scholar 

  210. Wen J, Mao HQ, Li WP, Lin KY, Leong KW (2004) J Pharm Sci 93:2142

    CAS  Google Scholar 

  211. Ahlheim M, Hallensleben ML, Wurm H (1986) Polym Bull 15:497

    CAS  Google Scholar 

  212. Ahlheim M, Hallensleben ML (1992) Makromol Chem 193:779

    CAS  Google Scholar 

  213. Hu XZ, Zhang Z, Zhang X, Li ZY, Zhu XX (2005) Steroids 70:531

    CAS  Google Scholar 

  214. Denike JK, Zhu XX (1994) Macromol Rapid Commun 15:459

    CAS  Google Scholar 

  215. Zhang YH, Zhu XX (1996) Macromol Chem Phys 197:3473

    CAS  Google Scholar 

  216. Zhu XX, Moskova M, Denike JK (1996) Polymer 37:493

    CAS  Google Scholar 

  217. Zhang YH, Akram M, Liu HY, Zhu XX (1998) Macromol Chem Phys 199:1399

    CAS  Google Scholar 

  218. Benrebouh A, Zhang YH, Zhu XX (2000) Macromol Rapid Commun 21:685

    CAS  Google Scholar 

  219. Benrebouh A, Avoce D, Zhu XX (2001) Polymer 42:4031

    CAS  Google Scholar 

  220. Zhang JH, Bazuin CG, Freiberg S, Brisse F, Zhu X (2005) Polymer 46:7266

    CAS  Google Scholar 

  221. Zhang X, Li Z, Zhu XX (2008) Biomacromolecules 9:2309

    CAS  Google Scholar 

  222. Liu HY, Avoce D, Song ZJ, Zhu XX (2001) Macromol Rapid Commun 22:675

    Google Scholar 

  223. Avoce D, Liu HY, Zhu XX (2003) Polymer 44:1081

    CAS  Google Scholar 

  224. Hao JQ, Li H, Zhu XX (2006) Biomacromolecules 7:995

    CAS  Google Scholar 

  225. Li Y, Zhang W, Li G, Ju Y (2008) Polymer 49:225

    CAS  Google Scholar 

Download references

Acknowledgements

Financial support by the Max Planck Society (MPG) and Firmenich International SA is acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Helmut Schlaad .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Zhao, J., Schlaad, H. (2011). Synthesis of Terpene-Based Polymers. In: Schlaad, H. (eds) Bio-synthetic Polymer Conjugates. Advances in Polymer Science, vol 253. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2012_166

Download citation

Publish with us

Policies and ethics